Electroluminescent Device

ABSTRACT

Disclosed are electroluminescent devices that comprise organic layers that contain certain organic compounds containing one ore more pyrimidine moieties. The organic compounds containing one ore more pyrimidine moieties are suitable components of blue-emitting, durable, organo-electroluminescent layers. The electroluminescent devices may be employed for full color display panels in for example mobile phones, televisions and personal computer screens.

This application is a continuation of pending U.S. application Ser. No.12/794,828 filed Jun. 7, 2010, which is a continuation of U.S.application Ser. No. 10/531,780 filed Apr. 19, 2005 and issued as U.S.Pat. No. 8,012,602 on Sep. 6, 2011, which is a national stage of PCT/EP2003/11637, filed Oct. 21, 2003, the contents of all foregoing documentsare herein incorporated by reference.

The present invention relates to organo-electroluminescent (EL) devices,in particular EL devices that comprise durable, blue-emittingorgano-electroluminescent layers. The organo-electroluminescent layerscomprise certain organic compounds containing one or more pyrimidinemoieties.

Progress has been made towards developing organic-basedelectroluminescent devices suitable for full color displays. Generally,an EL device is comprised of a light-emitting layer or layers and a pairof facing electrodes sandwiching the light-emitting layer(s).Application of an electric field between the electrodes results in theinjection of electrons and holes to the system, resulting in the releaseof energy as light.

However, organo EL devices have not been developed that have suitablestability under continuous operation. In particular, there remains aneed for blue-emitting, stable organo EL devices.

U.S. Pat. No. 5,104,740 teaches an electroluminescent element thatcomprises a fluorescent layer containing a coumarinic or azacoumarinicderivative and a hole transport layer, both made of organic compoundsand laminated on top of the other.

U.S. Pat. No. 6,280,859 discloses certain polyaromatic organic compoundsfor use as a light-emitting material in organo-electroluminescentdevices.

U.S. Pat. No. 5,116,708 is aimed at a hole transport material for ELdevices.

WO98/04007 and EP-A-1013740 relate to an electroluminescent arrangementwith the electron-conducting layer containing one or more compoundscomprising triazine as basic substance.

EP-A-1013740 discloses the use of triazine compounds in EL devices.

EP-A-1,202,608 discloses EL devices comprising a carbazole compound offormula

wherein R is

and X is C or N, which constitutes the hole transporting layer.

JP2002324678 relates to light emitting elements comprising at least onekind of compound of formula

whereinAr¹¹, Ar²¹ and Ar³¹ denote arylene groups, Ar¹², Ar²² and Ar³² denotesubstituents or hydrogen atoms, wherein at least one of Ar¹¹, Ar²¹,Ar³¹, Ar¹², Ar²² and Ar³² is either a condensed ring aryl structure or acondensed ring heteroaryl structure; Ar denotes an arylene group or aheteroarylene group; and at least one amine derivative having acondensed ring group with two or more rings are contained in a luminouslayer. As examples of compounds of the above formula, wherein Ar denotesa heteroarylene group the following two compounds are explicitlymentioned:

R is a group of formula

WO02/02714 relates to electroluminescent iridium compounds withfluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines anddevices made with such compounds.

U.S. Pat. No. 5,770,108 describes liquid crystal compositions comprisingpyrimidine compounds of the following formula

wherein Y is alkyl or —O-alkyl and liquid crystal element comprisingsaid composition.

WO01/05863 relates to EL devices comprising arylamine-substitutedpoly(arylene vinylenes).

JP2000347432 describes the use of

in EL devices.

EP-A-926216 relates to EL devices using triaryl amine compounds, such as

EP-A-690 053 relates to the use of conjugated compounds containing twoor more pyrimidine rings, which are part of the conjugated system, aselectroluminescent materials. The conjugated compounds described inEP-A-690 053 comprise pyrimidin-2,5-diyl groups which do not carrysubstituents at positions 4 and 6.

EP-A-563009 relates to EL devices comprising

as light emitting material.

U.S. Pat. No. 5,077,142 relates to EL devices comprising a number oforganic compounds as light emitting material. A pyrimidine moiety,

is listed among a long list of possible organic compounds.

It is the object of the present invention to provide a light emittingelement with excellent light emitting characteristics and durability.

Certain organic compounds containing one or more pyrimidine moieties arefound to be suitable for use in organo-electroluminescent devices. Inparticular, certain pyrimidine derivatives are suitable blue emitterswith good durability.

The present invention is aimed at an electroluminescent devicecomprising an organic light-emitting layer that contains at least oneblue-emitting organic compound containing one or more pyrimidinemoieties.

Accordingly the present invention relates to an electroluminescentdevice comprising an anode, a cathode and one or a plurality of organiccompound layers sandwiched therebetween, in which said organic compoundlayers comprise an organic compound containing one ore more pyrimidinemoieties:

For example, the present organic compounds comprise one, two, three ormore pyrimidine moieties, including oligomers. It is understood that theopen valences in the pyrimidine moiety represents a covalent bond thatis not limited in its substitution.

In general, the organic compound or compounds emit light below about 520nm, in particular between about 380 nm and about 520 nm.

The organic compound or compounds have especially a NTSC coordinate ofbetween about (0.12, 0.05) and about (0.16, 0.10), more especially aNTSC coordinate of about (0.14, 0.08).

The organic compound or compounds have a melting point above about 150°C., preferably above about 200° C. and most preferred above about 250°C.

For example, the organic compound is a pyrimidine compound of formula

whereinV is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, which can be substituted orunsubstituted, in particular

H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶;W is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, which can be substituted orunsubstituted, in particular

H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶;Y is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, which can be substituted orunsubstituted, in particular

H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶;X is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, which can be substituted orunsubstituted, in particular

H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶; wherein the groups V¹ to V⁵,W¹ to W⁵, X¹ to X⁵ and Y¹ to Y⁵ are independently of each other H;halogen, C₆-C₂₄aryl; C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl;C₁-C₁₈alkyl which is substituted by E and/or interrupted by D;C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by Eand/or interrupted by D;

wherein Ar¹ is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, especially phenyl, Ar² isC₆-C₃₀aryl or C₂-C₃₀heteroaryl, especially phenyl, or H, C₂-C₁₈alkynyl;C₂-C₁₈alkynyl which is substituted by E and/or interrupted by D;C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is substituted by E and/or interruptedby D; —SR⁵; —NR⁵R⁶; C₂-C₂₄ hetero-aryl; C₂-C₂₄heteroaryl which issubstituted by L; —SOR⁴; —SO₂R⁴; —COR^(B); —COOR⁷; —CONR⁵R⁶;C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which is substituted by E and/orinterrupted by D; C₄-C₁₈cycloalkenyl; C₄-C₁₈cycloalkenyl which issubstituted by E and/or interrupted by D; orW⁵ or Y⁵ together with V form a group —CR⁹ ₂—, —CR⁹ ₂—CR⁹ ₂—, —C(═O)CR⁹₂—, —C(═O)—, or —CR⁹═CR⁹—, orW⁵ and Y⁵ together with V form a group

wherein R⁹ is H; C₁-C₁₈alkyl, C₁-C₁₈alkyl which is interrupted by —O—,C₆-C₁₈aryl, C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl, orC₁-C₁₈alkoxy, orone of the substituents V, W, X, or Y is a group of the formula —Z,—Ar—Z, wherein Ar is C₆-C₂₄aryl or C₂-C₂₄heteroaryl, which can besubstituted, in particular

wherein Z is a group of formula

one of the substituentsV¹ to V⁵, W¹ to W⁵, X¹ to X⁵, or Y¹ to Y⁵ is a group of the formula —Z′,—Ar—Z′, wherein Ar is C₆-C₂₄aryl or C₂-C₂₄heteroaryl, which can besubstituted, in particular

wherein Z′ is a group of formula

whereinA¹, B¹ and B² are independently of each other H; C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substitutedby E and/or interrupted by D; C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which issubstituted by E and/or interrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenylwhich is substituted by E and/or interrupted by D; C₂-C₁₈alkynyl;C₂-C₁₈alkynyl which is substituted by E and/or interrupted by D;C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is substituted by E and/or interruptedby D; —SR⁵; —NR⁵R⁶; C₂-C₁₈heteroaryl; C₂-C₁₈heteroaryl which issubstituted by L; —SOR⁴; —SO₂R⁴; —COR^(B); —COOR⁷; —CONR⁵R⁶;C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which is substituted by E and/orinterrupted by D; C₄-C₁₈cycloalkenyl; C₄-C₁₈cycloalkenyl which issubstituted by E and/or interrupted by D; ortwo substituents A¹, B¹, B² or B¹ and B² form a five to seven memberedring, which can be substituted,m is an integer of 1 to 4; and W¹, W², Y¹, Y², X¹, X², V, W, X and Y areas defined above;D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; —SiR⁵R⁶—;—POR⁵—; —CR⁵═CR⁶—; or —C≡C—;E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —CONR⁵R⁶; —CN; —OCOOR⁷; orhalogen, especially F;G is E; K; heteroaryl; heteroaryl which is substituted by C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by E and/or K;K is C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D; C₇-C₁₈alkylaryl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by Eand/or interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which issubstituted by E and/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxywhich is substituted by E and/or interrupted by D; C₄-C₁₈cycloalkyl;C₄-C₁₈cycloalkyl which is substituted by E and/or interrupted by D;C₄-C₁₈cycloalkenyl; or C₄-C₁₈cycloalkenyl which is substituted by Eand/or interrupted by D;L is E; K; C₆-C₁₈aryl; or C₆-C₁₈aryl which is substituted by G, E and/orK;R⁴ is C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—;R⁵ and R⁶ are independently of each other H; C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; C₁-C₁₈alkyl; orC₁-C₁₈alkyl which is interrupted by —O—; orR⁵ and R⁶ together form a five or six membered ring, in particular

R⁷ is H; C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is interrupted by —O—;R⁸ is H; C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is interrupted by —O—.or two substituents selected from V¹ to V⁵, W¹ to W⁵, X¹ to X⁵, Y¹ to Y⁵which are in neighborhood to each other form a five to seven memberedring.

Preferably at least one, more preferably at least two, most preferablyat least three of the groups V, W, X and Y are C₆-C₃₀aryl orC₂-C₃₀heteroaryl, which optionally can be substituted.

Preferred are compounds of formula I, wherein Y is

wherein Y¹ to Y⁵ are as defined above and at least one of thesubstituents Y¹ to Y⁵ is different from H; W is

wherein W¹ to W⁵ are as defined above and at least one of thesubstituents W¹ to W⁵ is different from H; X is

wherein X¹ to X⁵ are as defined above and at least one of thesubstituents X¹ to X⁵ is different from H, and/or V is

wherein V¹ to V⁵ are as defined above and at least one substituent V¹ toV⁵ is different from H.

In one further embodiment compounds of formula I are preferred, whereinY is

and

W is

wherein W¹ and W⁵ and Y¹ and Y⁵ are independently of each other H;C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is substituted by E and/or interruptedby D.

Examples of suitable groups Ar are

especially

especially

especially

especially

whereinn1, n2, n3, n4, n5, n6 and n7 are integers of 1 to 10, in particular 1to 3,A⁶ and A⁷ are independently of each other H, C₁-C₁₈alkyl, C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D, C₆-C₂₄aryl,C₆-C₂₄aryl which is substituted by E, C₂-C₂₀heteroaryl, C₂-C₂₀heteroarylwhich is substituted by E, C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₁-C₁₈alkoxy,C₁-C₁₈alkoxy which is substituted by E and/or interrupted by D,C₇-C₂₅aralkyl, or —CO—R²⁸,A⁸ is C₁-C₁₈alkyl, C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D, C₆-C₂₄ aryl, or C₇-C₂₅aralkyl,A⁹ and A¹⁰ are independently of each other C₁-C₁₈ alkyl, C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D, C₆-C₂₄aryl,C₆-C₂₄aryl which is substituted by E, C₂-C₂₀heteroaryl, C₂-C₂₀heteroarylwhich is substituted by E, C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₁-C₁₈alkoxy,C₁-C₁₈alkoxy which is substituted by E and/or interrupted by D, orC₇-C₂₅aralkyl, orA⁹ and A¹⁰form a ring, especially a five- or six-membered ring,A¹⁴ and A¹⁵ are independently of each other H, C₁-C₁₈alkyl, C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D, C₆-C₂₄aryl,C₆-C₂₄aryl which is substituted by E, C₂-C₂₀heteroaryl, orC₂-C₂₀heteroaryl which is substituted by E,D is —CO—; —COO—; —S—; —SO—; —SO₂—; —O—; —NA²⁵-; —SiA³⁰A³¹-; —POA³²-;—CA²³=CA²⁴-; or —C≡C—; andE is —OA²⁹; —SA²⁹; —NA²⁵A²⁶; —COA²⁸; —COOA²⁷; —CONA²⁵A²⁶; —CN; —OCOOA²⁷;or halogen;wherein A²³, A²⁴, A²⁵ and A²⁶ are independently of each other H;C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—;or A²⁵ and A²⁶ together form a five or six membered ring, in particular

A²⁷ and A²⁸ are independently of each other H; C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, or C₁-C₁₈alkoxy; C₁-C₁₈alkyl; orC₁-C₁₈alkyl which is interrupted by —O—,A²⁹ is H; C₆-C₁₈aryl; C₆-C₁₈aryl, which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—,A³⁰ and A³¹ are independently of each other C₁-C₁₈alkyl, C₆-C₁₈aryl, orC₆-C₁₈aryl, which is substituted by C₁-C₁₈alkyl, andA³² is C₁-C₁₈alkyl, C₆-C₁₈aryl, or C₆-C₁₈aryl, which is substituted byC₁-C₁₈alkyl.

Preferably, A⁶ and A⁷ are independently of each other H, C₁-C₁₈alkyl,such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl,sec-butyl, t-butyl, 2-methylbutyl, n-pentyl, isopentyl, n-hexyl,2-ethylhexyl, or n-heptyl, C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D, such as —CH₂OCH₃, —CH₂OCH₂CH₃, —CH₂OCH₂CH₂OCH₃, or—CH₂OCH₂CH₂OCH₂CH₃, C₆-C₂₄aryl, such as phenyl, naphthyl, or biphenyl,C₆-C₂₄aryl which is substituted by E, such as —C₆H₄OCH₃, —C₆H₄OCH₂CH₃,—C₆H₃(OCH₃)₂, or —C₆H₃(OCH₂CH₃)₂, —C₆H₄CH₃, —C₆H₃(CH₃)₂, —C₆H₂(CH₃)₃, or—C₆H₄tBu.

A⁸ is preferably H, C₁-C₁₈alkyl, such as methyl, ethyl, n-propyl,iso-propyl, n-butyl, isobutyl, sec-butyl, t-butyl, 2-methylbutyl,n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, n-heptyl, or C₆-C₂₄aryl,such as phenyl, naphthyl, or biphenyl.

Preferably, A⁹ and A¹⁰ are independently of each other H, C₁-C₁₈alkyl,such as n-butyl, sec-butyl, hexyl, octyl, or 2-ethyl-hexyl, C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D, such as—CH₂(OCH₂CH₂)_(w)OCH₃, w=1, 2, 3, or 4, C₆-C₂₄aryl, such as phenyl,naphthyl, or biphenyl, C₆-C₂₄aryl which is substituted by E, such as—C₆H₄OCH₃, —C₆H₄OCH₂CH₃, —C₆H₃(OCH₃)₂, —C₆H₃(OCH₂CH₃)₂, —C₆H₄CH₃,—C₆H₃(CH₃)₂, —C₆H₂(CH₃)₃, or —C₆H₄tBu, or A⁹ and A¹⁰ together form a 4to 8 membered ring, especially a 5 or 6 membered ring, such ascyclohexyl, or cyclopentyl.

Preferably, A¹⁴ and A¹⁵ are independently of each other H, C₁-C₁₈alkyl,such as as methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, orsec-butyl, or C₆-C₂₄aryl, such as phenyl, naphthyl, or biphenyl.

D is preferably —CO—, —COO—, —S—, —SO—, —SO₂—, —O—, —NA²⁵-, wherein A²⁵is C₁-C₁₈alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl,isobutyl, or sec-butyl, or C₆-C₂₄aryl, such as phenyl, naphthyl, orbiphenyl.

E is preferably —OA²⁹; —SA²⁹; —NA²⁵A²⁵; —COA²⁸; —COOA²⁷; —CONA²⁵A²⁵; or—CN; wherein A²⁵, A²⁷, A²⁸ and A²⁹ are independently of each otherC₁-C₁₈ alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl,isobutyl, sec-butyl, hexyl, octyl, or 2-ethyl-hexyl, or C₆-C₂₄ aryl,such as phenyl, naphthyl, or biphenyl.

Among the above-mentioned Ar the following groups are preferred:

wherein the substituents are defined as above.

Preferably the electroluminescent device comprises pyrimidine compoundsof formula I to VI:

wherein V, W, Y and X¹ to X⁵ are as defined above;

wherein V, X, Y and W¹ to W⁵ are as defined above, especially

Y is R¹, if X is

or X is R¹, if Y is

wherein R¹ is H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which issubstituted by E and/or interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynylwhich is substituted by E and/or interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is substituted by E and/or interrupted by D; —SR⁵; or—NR⁵R⁶; wherein W¹ to W⁵, X¹ to X⁵, Y¹ to Y⁵, E, D, R⁵ and R⁶ are asdefined above, wherein most preferred W¹ and W⁵ and Y¹ and Y⁵ areindependently of each other H; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which issubstituted by E and/or interrupted by D;

wherein V, W¹ to W⁵, X¹ to X⁵ and Y¹ to Y⁵ are as defined above,preferably W³, X³ and Y³ are selected from the group consisting ofC₆-C₂₄aryl; C₆-C₂₄aryl which is substituted by G; C₂-C₂₄heteroaryl;C₂-C₂₄heteroaryl which is substituted by L, C₁-C₁₈alkoxy, —SR⁵; —NR⁵R⁶,wherein G, L, R⁵ and R⁶ are as defined above, V is H and/or W¹ and W⁵,Y¹ and Y⁵ as well as X¹ and X⁵ are independently of each other H;C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is substituted by E and/or interruptedby D, wherein E and D are as defined above; or

whereinAr is a group of formula

especially

W¹¹ to W¹⁵, W²¹ to W²⁵, W³¹ to W³⁵, W⁴¹ to W⁴⁵, Y¹¹ to Y¹⁵, Y²¹ to Y²⁵,Y³¹ to Y³⁵ and Y⁴¹ to Y⁴⁵ are independently of each other H; C₆-C₂₄aryl;C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which issubstituted by E and/or interrupted by D; C₇-C₁₈alkylaryl;C₇-C₁₈alkylaryl which is substituted by E and/or interrupted by D;C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶; C₂-C₂₄heteroaryl;C₂-C₂₄heteroaryl which is substituted by L; —SOR⁴; —SO₂R⁴; —COR⁸;—COOR⁷; —CONR⁵R⁶; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which issubstituted by E and/or interrupted by D; C₄-C₁₈cycloalkenyl;C₄-C₁₈cycloalkenyl which is substituted by E and/or interrupted by D;V is H; C₆-C₂₄aryl; C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl;C₁-C₁₈alkyl which is substituted by E and/or interrupted by D;C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by Eand/or interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which issubstituted by E and/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxywhich is substituted by E and/or interrupted by D; —SR⁵; or —NR⁵R⁶;C₂-C₂₄heteroaryl; C₂-C₂₄heteroaryl which is substituted by L; —SOR⁴;—SO₂R⁴; —COR^(B); —COOR⁷; —CONR⁵R⁶; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkylwhich is substituted by E and/or interrupted by D; C₄-C₁₈cycloalkenyl;C₄-C₁₈cycloalkenyl which is substituted by E and/or interrupted by D;A¹⁸ and A¹⁹ are independently of each other H, C₁-C₁₈alkyl; C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D; C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by E,B¹¹ to B¹⁴ and B²¹ to B²⁴ are independently of each other H; C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which issubstituted by E and/or interrupted by D; C₇-C₁₈alkylaryl;C₇-C₁₈alkylaryl which is substituted by E and/or interrupted by D;C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶; C₂-C₁₈heteroaryl;C₂-C₁₈heteroaryl which is substituted by L; —SOR⁴; —SO₂R⁴; —COR^(B);—COOR⁷; or —CONR⁵R⁶; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which issubstituted by E and/or interrupted by D; C₄-C₁₈cycloalkenyl;C₄-C₁₈cycloalkenyl which is substituted by E and/or interrupted by D;wherein D, E, G, L, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined above, and V informula VI or VII is preferably H.

Moreover, pyrimidine compounds of formula I are preferred, wherein V isa group of the formula

H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; or —NR⁵R⁶; and/orW is a group of the formula

in particular

H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; or —NR⁵R⁶; wherein W¹ to W⁵, D, V¹to V⁵, E, A¹, B¹, B², R⁵, R⁶, m and Z are as defined above and R¹⁰¹ andR¹⁰² are independently of each other H, C₁-C₈alkyl, C₆-C₂₄aryl, orC₅-C₇cycloalkyl, in particular H or C₁₋₄-alkyl.

The compounds of general formula IV, VI and VII are novel and form afurther subject of the present application.

In one preferred embodiment the present invention is directed topyrimidine compounds of formula

whereinat least one of the groups W, X and Y is a group of formula

and the other groups are independently of each other an aryl group or aheteroaryl group, especially a group of formula

whereinR¹¹, R^(11′), R¹², R^(12′), R¹³, R^(13′), R¹⁵, R^(15′), R¹⁶, R^(16′),R¹⁷, R^(17′), R⁴¹, R^(41′), R⁴², R^(42′), R⁴⁴, R^(44′), R⁴⁵, R^(45′),R⁴⁶, R^(46′), R⁴⁷ and R^(47′) are independently of each other H, E,C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by E; C₁-C₁₈alkyl;C₁-C₁₈alkyl which is substituted by E and/or interrupted by D;C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which is substituted by E; orR^(11′) and R¹², R^(12′) and R¹³, R^(15′) and R¹⁶, R^(16′) and R¹⁷,R^(44′) and R⁴⁶ and/or R^(45′) and R⁴⁷ are each a divalent group L¹selected from an oxygen atom, an sulfur atom, >CR¹¹⁸R¹¹⁹>SiR¹¹⁸R¹¹⁹, or

whereinR¹¹⁸ and R¹¹⁹ are independently of each other C₁-C₁₈alkyl; C₁-C₁₈alkoxy,C₆-C₁₈aryl; C₇-C₁₈aralkyl;R¹¹ and R^(11′), R¹² and R^(12′), R¹³ and R^(13′), R^(13′) and R¹⁴, R¹⁴and R¹⁵, R¹⁵ and R^(15′), R¹⁶ and R^(16′), R^(17′) and R¹⁷, R⁴¹ andR^(41′), R⁴² and R^(42′), R^(42′) and R⁴³, R^(41′) and R⁴³, R⁴⁴ andR^(44′), R⁴⁵ and R^(45′). R⁴⁶ and R^(46′), R⁴⁷ and R^(47′), R^(46′) andR⁴⁸ and/or R^(47′) and R⁴⁸ are each a divalent group

whereinR³⁰, R³¹, R³², R³³, R⁴⁹ and R⁵⁰ are independently of each other H,C₁-C₁₈alkyl; C₁-C₁₈alkyl, which is substituted by E and/or interruptedby D; E; C₆-C₁₈aryl; C₆-C₁₈aryl, which is substituted by E;R¹⁴ is H, C₂-C₃₀heteroaryl, C₆-C₃₀aryl, or C₆-C₃₀aryl which issubstituted by E, C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; especially

wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶ and R²⁷ are independently of eachother H, E, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D; E; C₇-C₁₈aralkyl; C₇-C₁₈aralkyl which is substitutedby E;R⁴³ and R⁴⁸ are independently of each other H, E; C₁-C₁₈alkyl;C₁-C₁₈alkyl, which is substituted by E and/or interrupted by D;C₂-C₃₀heteroaryl; C₇-C₁₈aralkyl; C₇-C₁₈aralkyl which is substituted byE;D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; SiR⁵R⁶—; —POR⁵—;—CR⁹═CR¹⁰—; or —C≡C—;E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR^(B); —COOR⁷; —CONR⁵R⁶; —CN; or halogen,especially F, or Cl;wherein R⁵ and R⁶ are independently of each other C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkyl; or C₁-C₁₈alkyl whichis interrupted by —O—; orR⁵ and R⁶ together form a five or six membered ring, in particular

R⁷ is C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—;R⁸ is C₇-C₁₂alkylaryl; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interruptedby —O—; andR⁹ and R¹⁰ are independently of each other H, C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkyl; or C₁-C₁₈alkyl whichis interrupted by —O—.W is preferably a group of formula

whereinR¹³, R^(13′), R¹⁵ and R^(15′) are H and R²⁰ is H, especially

orR¹³ and R¹⁵ are H, R^(13′) and R¹⁵ are independently of each other H,C₁-C₈alkyl, or C₁-C₈alkoxy, and R²⁰ is H, C₁-C₈alkyl, or C₁-C₈alkoxy; orR¹³, R¹⁵ and R^(15′) are H, and R^(13′) and R²⁰ are

R²⁰, R¹⁵ and R^(15′) are H, and R¹³ and R^(13′) are

whereinR³⁰, R³¹, R³² and R³³ are H, C₁-C₈alkyl, or C₁-C₈alkoxy, andX and Y are as defined above.

According to the present invention at least one of the groups W, X andY, preferably two of the groups W, X and Y, most preferred all threegroups W, X and Y are a group of formula

Accordingly, in one preferred embodiment of the present invention thepyrimidine compound is a compound of formula I, wherein W and Y or W andX (=X and Y) are independently of each other a group of formula

especially

andX is a group of formula

especially,

wherein R¹¹, R^(11′), R¹², R^(12′), R¹³, R^(13′), R¹⁴, R¹⁵, R^(15′),R¹⁶, R^(16′), R¹⁷, R^(17′), R⁴¹, R^(41′), R⁴², R^(42′), R⁴⁴, R^(44′),R⁴⁵, R^(45′), R⁴⁶, R^(46′), R⁴⁷, R^(47′), R⁴³ and R⁴⁸ are as definedabove, especially H, C₁-C₈alkyl, C₁-C₈alkoxy, or phenyl.R¹¹, R^(11′), R¹², R^(12′), R¹³, R^(13′), R¹⁵, R^(15′), R¹⁶, R^(16′),R¹⁷ and R^(17′), R⁴¹, R^(41′), R⁴², R^(42′), R⁴⁴, R^(44′), R⁴⁵, R^(45′),R⁴⁶, R^(46′), R⁴⁷, and R^(47′) as well as R¹⁴, R⁴³, and R⁴⁸ arepreferably independently of each other H, E; or C₁-C₈alkyl, especiallyH, C₁-C₄alkyl, C₁-C₄alkoxy, or phenyl; wherein E is —OR⁵; —SR⁵; —NR⁵R⁶;—COR^(B); —COOR⁷; —CONR⁵R⁶; —CN; —OCOOR⁷; or halogen, especially F;wherein R⁵ and R⁶ are independently of each other C₆-C₁₂ary, orC₁-C₈alkyl;R⁷ is C₇-C₁₂ alkylaryl, or C₁-C₈alkyl; andR⁸ is C₆-C₁₂aryl; or C₁-C₈alkyl, orR¹¹ and R^(11′), R¹² and R^(12′), R¹³ and R^(13′), R¹³ and R¹⁴, R⁴¹ andR^(41′), R^(41′) and R⁴³, R⁴⁴ and R^(44′), R⁴⁶ and R^(46′), R^(46′) andR⁴⁸ and/or R^(47′) and R⁴⁸ are each a divalent group

In one more preferred embodiment of the present invention W, X and Y areindependently of each other a group of formula

whereinR¹¹, R^(11′), R¹², R^(12′), R¹³, R^(13′), R¹⁵, R^(15′), R¹⁶, R^(16′),R¹⁷ and R^(17′) are independently of each other H, C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by E; E, C₁-C₁-C₁₈alkyl; C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D; C₇-C₁₈aralkyl;C₇-C₁₈aralkyl which is substituted by E; and R¹⁴, R¹⁸ and R¹⁹ are asdefined above, orW is a group of the formula —W¹—W²—W³X is a group of the formula —X¹—X²—X³ and/orY is a group of the formula —Y¹—Y²—Y³, wherein W¹, W², X¹, X², Y¹ and Y²are independently of each other a group of formula

and W³, X³ and Y³ are independently of each other a group of formula

wherein R¹⁴ is as defined above.

W, X and Y can be different, but have preferably the same meaning.

Pyrimidine compounds of formula I are preferred, wherein R¹¹, R^(11′),R¹², R^(12′), R¹³, R^(13′), R¹⁵, R^(15′), R¹⁶, R^(16′), R¹⁷ and R^(17′),R⁴¹, R^(41′), R⁴², R^(42′), R⁴⁴, R^(44′), R⁴⁵, R^(45′), R⁴⁶, R^(46′),R⁴⁷, and R^(47′) are independently of each other H, E; or C₁-C₈alkyl;wherein

E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —CONR⁵R⁶; —CN; —OCOOR⁷; orhalogen; wherein R⁵ and R⁶ are independently of each other C₆-C₁₂aryl;or C₁-C₈alkyl;R⁷ is C₇-C₁₂ alkylaryl, or C₁-C₈alkyl; andR⁸ is C₆-C₁₂aryl, or C₁-C₈alkyl.

Especially preferred are pyrimidine compounds of formula I, wherein

W, X and Y are independently of each other a group of formula

wherein R¹³, R^(13′), R¹⁵ and R^(15′) are H and R²⁰ is H, especially

orR¹³ and R¹⁵ are H, R^(13′) and R^(15′) are independently of each otherH, C₁-C₈alkyl, or C₁-C₈alkoxy, and R²⁰ is H, C₁-C₈alkyl, or C₁-C₈alkoxy;orR¹³, R¹⁵ and R^(15′) are H, and R^(13′) and R²⁰ are

orR²⁰, R¹⁵ and R^(15′) are H, and R¹³ and R^(13′) are

whereinR³⁰, R³¹, R³² and R³³ are H, C₁-C₈alkyl, or C₁-C₈alkoxy; or whereinW, X and Y are independently of each other a group of formula

wherein R¹⁸ and R¹⁹ are independently of each other C₁-C₈alkyl.

In a further preferred embodiment the present invention is directed topyrimidine compounds of formula

whereinAr is a group of formula

especially

W¹¹ to W¹⁵, W²¹ to W²⁵, W³¹ to W³⁵, W⁴¹ to W⁴⁵, Y¹¹ to Y¹⁵, Y²¹ to Y²⁵,Y³¹ to Y³⁵ and Y⁴¹ to Y⁴⁵ are independently of each other H; C₆-C₂₄aryl;C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which issubstituted by E and/or interrupted by D; C₇-C₁₈alkylaryl;C₇-C₁₈alkylaryl which is substituted by E and/or interrupted by D;C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is substituted by Eand/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is substitutedby E and/or interrupted by D; —SR⁵; —NR⁵R⁶; C₂-C₂₄heteroaryl;C₂-C₂₄heteroaryl which is substituted by L; —SOR⁴; —SO₂R⁴; —COR⁸;—COOR⁷; —CONR⁵R⁶; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which issubstituted by E and/or interrupted by D; C₄-C₁₈cycloalkenyl;C₄-C₁₈cycloalkenyl which is substituted by E and/or interrupted by D;V is H; C₆-C₂₄aryl; C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl;C₁-C₁₈alkyl which is substituted by E and/or interrupted by D;C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by Eand/or interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which issubstituted by E and/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxywhich is substituted by E and/or interrupted by D; —SR⁵; or —NR⁵R⁶;C₂-C₂₄heteroaryl; C₂-C₂₄heteroaryl which is substituted by L; —SOR⁴;—SO₂R⁴; —COR^(B); —COOR⁷; —CONR⁵R⁶; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkylwhich is substituted by E and/or interrupted by D; C₄-C₁₈cycloalkenyl;C₄-C₁₈cycloalkenyl which is substituted by E and/or interrupted by D;A¹⁸ and A¹⁹ are independently of each other H, C₁-C₁₈alkyl; C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D; C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by E,B¹¹ to B¹⁴, B²¹ to B²⁴, B³¹ to B³⁴ and B⁴¹ to B⁴⁴ are independently ofeach other H; C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by G;C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/or interrupted byD; C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is substituted by E and/orinterrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is substituted by Eand/or interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which issubstituted by E and/or interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxywhich is substituted by E and/or interrupted by D; —SR⁵; —NR⁵R⁶;C₂-C₁heteroaryl; C₂-C₁₈heteroaryl which is substituted by L; —SOR⁴;—SO₂R⁴; —COR^(B); —COOR⁷; or —CONR⁵R⁶; C₄-C₁₈cycloalkyl;C₄-C₁₈cycloalkyl which is substituted by E and/or interrupted by D;C₄-C₁₈cycloalkenyl; C₄-C₁₈cycloalkenyl which is substituted by E and/orinterrupted by D; wherein D, E, G, L, R⁴, R⁵, R⁶, R⁷ and R³ are asdefined above.

In a preferred embodiment W and Y are groups of the formula

Particularly preferred are pyrimidine compounds of the followingformula:

wherein V is H, or C₁-C₈-alkyl,X³ and X⁴ are independently of each other H, C₁-C₈alkyl, C₁-C₈alkoxy,C₁-C₈thioalkyl, or phenyl,X⁵ is H, or C₁-C₈alkoxy,W⁵ is H, C₁-C₈alkyl, or O(CH₂)_(n1)—X,Y⁵ is H, C₁-C₈alkyl, or O(CH₂)_(n1)—X,Y³, Y⁴, W³ and W⁴ are independently of each other C₁-C₈alkyl,C₁-C₈alkoxy, C₁-C₈thioalkyl, halogen, in particular Br, phenyl, orO(CH₂)_(n1)—X, wherein n1 is an integer of 1 to 5 and X is—O—(CH₂)_(m1)CH₃, —OC(O)—(CH₂)_(m1)CH₃, —C(O)—O—C₁-C₈alkyl, —NR¹⁰³R¹⁰⁴,wherein m1 is an integer of 0 to 5 and R¹⁰³ and R¹⁰⁴ are independentlyof each other H, or C₁-C₈-alkyl, or R¹⁰³ and R¹⁰⁴ together form a fiveor six membered heterocyclic ring, in particular

wherein V is H, or C₁-C₈alkyl,W³ is H, C₁-C₈alkyl, or C₁-C₈alkoxy,X³ is H, C₁-C₈alkoxy, phenyl or O(CH₂)_(n1)—X,X⁵ is H, C₁-C₈alkoxy, phenyl or O(CH₂)_(n1)—X,Y³ is H, C₁-C₈alkyl, or C₁-C₈alkoxy, wherein n1 is an integer of 1 to 4and X is —O—(CH₂)_(m1)CH₃, —OC(O)—(CH₂)_(m1)CH₃, —C(O)—O—C₁-C₈alkyl,wherein m1 is an integer of 0 to 5;

wherein W³ and W⁴are independently of each other H, —NR¹⁰³R¹⁰⁴,C₁-C₈thioalkyl, or C₁-C₈alkoxy,Y³ and Y⁴are independently of each other H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl,or C₁-C₈alkoxy, wherein R¹⁰³ and R¹⁰⁴ are independently of each other H,or C₁-C₈alkyl.W⁵ is H, C₁-C₈alkyl, or O(CH₂)_(n1)—X,Y⁵ is H, C₁-C₈alkyl, or O(CH₂)_(n1)—X,wherein n1 is an integer of 1 to 5 and X is —O—(CH₂)_(m1)CH₃,—OC(O)—(CH₂)_(m1)CH₃, —C(O)—O—C₁-C₈alkyl, —NR¹⁰³R¹⁰⁴, wherein m1 is aninteger of 0 to 5 and R¹⁰³ and R¹⁰⁴ are independently of each other H,or C₁-C₈-alkyl, or R¹⁰³ and R¹⁰⁴ together form a five or six memberedheterocyclic ring, in particular

wherein V, W¹ to W⁵, X, Y¹ to Y⁵ are as defined above, wherein V ispreferably

with the proviso that at least one substituent V¹ to V⁵ is differentfrom hydrogen;

wherein X, Y, W¹ to W⁴, and R⁹ are as defined above;

wherein W³ is H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl, or C₁-C₈alkoxy,Y³ is H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl, or C₁-C₈alkoxy, wherein R¹⁰³ andR¹⁰⁴ are independently of each other H, or C₁-C₈alkyl,R¹⁰¹ and R¹⁰² are independently of each other H, C₁-C₈alkyl, phenyl, orC₅-C₇cycloalkyl, in particular cyclohexyl;

wherein Y³ is H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl, or C₁-C₈alkoxy,X³ is H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl, or C₁-C₈alkoxy, wherein R¹⁰³ andR¹⁰⁴ are independently of each other H, or C₁-C₈alkyl;

Y³ is H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl, or C₁-C₈alkoxy,X³ is H, —NR¹⁰³R¹⁰⁴, C₁-C₈thioalkyl, or C₁-C₈alkoxy, wherein R¹⁰³ andR¹⁰⁴ are independently of each other H, or C₁-C₈alkyl, R¹⁰¹ and R¹⁰² areindependently of each other H, C₁-C₈alkyl, phenyl, or C₅-C₇cycloalkyl,in particular cyclohexyl;pyrimidine compounds of formula

wherein W³ and Y³ are a group of formula

wherein R¹¹⁰ is C₆-C₁₀-aryl, such as phenyl, 1-naphthyl, 2-naphthyl, 3-or 4-biphenyl, 9-phenanthryl, 2- or 9-fluorenyl, which is optionallysubstituted by C₁-C₆-alkyl, or C₁-C₄-alkoxy, especially

or C₄-C₁₀ heteroaryl, especially

andX³ is H, C₁-C₆-alkyl, C₁-C₄-alkoxy, Ph, or

andpyrimidine compounds of formula I, whereinV is hydrogen,W and Y are independently of each other a group of formula

andX is a group of formula

whereinR¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently of each other H,C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by E; E, C₁-C₁₈alkyl;C₁-C₁₈alkyl which is substituted by E and/or interrupted by D;C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by E;R¹⁸ and R¹⁹ are independently of each other H, C₁-C₁₈alkyl; C₁-C₁₈alkylwhich is substituted by E and/or interrupted by D; C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by E;D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; —SiR⁵R⁶—;—POR⁵—; —CR⁵═CR⁶—; or —C≡C—;E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —CONR⁵R⁶; —CN; —OCOOR⁷; orhalogen; whereinR⁵, R⁶, R⁷ and R⁸ are as defined above, wherein pyrimidine compounds offormula I, whereinV is hydrogen,W and Y are a group of formula

andX is a group of formula

or are most preferred.

The present pyrimidine compounds are known or can be prepared accordingto or analogous to known procedures. The present pyrimidine compoundsare for instance derivatives of known hydroxyphenyl pyrimidinecompounds: U.S. Pat. Nos. 3,442,898, 5,597,854 and 5,753,729, therelevant parts of which are hereby incorporated by reference. Thepresent pyrimidine compounds can for instance be prepared according toor analogous to the following procedures (Suzuki aryl-aryl crosscoupling reaction: Chem. Commun., 2002, 874-875; DE-A-3001188, J. Org.Chem. Vol. 36, 1971, 3382-3385):

An amidine hydrochloride is added to a 2-propen-1-one derivative in aC₁-C₄-alcohol, like methanol, ethanol, propanol or butanol. A base, forexample, an alkali metal hydroxide or alkoxide, such as sodium methoxideor potassium hydroxide is added and the solution is stirred in thepresence of oxygen, for example dry air.

The pyrimidine compounds of the present invention, comprising thefollowing units:

can be prepared according to a process, which comprises reacting aderivative of formula

wherein X⁶, V, W⁶, Y⁶ and m are as defined above,R¹⁰⁰ stands for halogen such as chloro or bromo, preferably bromo, or Ehaving the meaning of

wherein a is 2 or 3,with boronic acid derivative

E-Ar,

or—in case R¹⁰⁰ is not halogen—

Hal-Ar,

wherein Hal stands for halogen, preferably for bromo,wherein Ar is C₆-C₃₀-aryl or C₂-C₃₀-heteroaryl, which can besubstituted, in the presence of an allylpalladium catalyst of thep-halo(triisopropylphosphine)(η³-allyl)palladium(II) type (see forexample WO99/47474).

Preferably, the reaction is carried out in the presence of an organicsolvent, such as an aromatic hydrocarbon or a usual polar organicsolvent, such as benzene, toluene, xylene, tetrahydrofurane, or dioxane,or mixtures thereof, most preferred toluene. Usually, the amount of thesolvent is chosen in the range of from 1 to 10 l per mol of boronic acidderivative. Also preferred, the reaction is carried out under an inertatmosphere such as nitrogen, or argon. Further, it is preferred to carryout the reaction in the presence of an aqueous base, such as an alkalimetal hydroxide or carbonate such as NaOH, KOH, Na₂CO₃, K₂CO₃, Cs₂CO₃and the like, preferably an aqueous K₂CO₃ solution is chosen. Usually,the molar ratio of the base to compound III is chosen in the range offrom 0.5:1 to 50:1.

Generally, the reaction temperature is chosen in the range of from 40 to180° C., preferably under reflux conditions.

Preferred, the reaction time is chosen in the range of from 1 to 80hours, more preferably from 20 to 72 hours.

In a preferred embodiment a usual catalyst for coupling reactions or forpolycondensation reactions is used, preferably Pd-based catalyst such asknown tetrakis(triarylphosphonium)-palladium, preferably (Ph₃P)₄Pd andderivatives thereof. Usually, the catalyst is added in a molar ratiofrom inventive DPP polymer to the catalyst in the range of from 100:1 to10:1, preferably from 50:1 to 30:1.

Also preferred, the catalyst is added as in solution or suspension.Preferably, an appropriate organic solvent such as the ones describedabove, preferably benzene, toluene, xylene, THF, dioxane, morepreferably toluene, or mixtures thereof, is used. The amount of solventusually is chosen in the range of from 1 to 10 l per mol of boronic acidderivative.

The obtained inventive polymer can be isolated by well-known methods.Preferably, after cooling down the reaction mixture to room temperature,it is poured into acetone and the obtained precipitation is filteredoff, washed and dried.

C₁-C₁₈alkyl is a branched or unbranched radical such as for examplemethyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl,tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl,1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl,1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl,2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl,decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl,tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, or octadecyl.

C₁-C₁₈Alkoxy radicals are straight-chain or branched alkoxy radicals,e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy,isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy,pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy.

C₂-C₁₈Alkenyl radicals are straight-chain or branched alkenyl radicals,such as e.g. vinyl, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl,isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl,n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl.

C₂₋₂₄Alkynyl is straight-chain or branched and preferably C₂₋₈alkynyl,which may be unsubstituted or substituted, such as, for example,ethynyl, 1-propyn-3-yl, 1-butyn-4-yl, 1-pentyn-5-yl,2-methyl-3-butyn-2-yl, 1,4-pentadiyn-3-yl, 1,3-pentadiyn-5-yl,1-hexyn-6-yl, cis-3-methyl-2-penten-4-yn-1-yl,trans-3-methyl-2-penten-4-yn-1-yl, 1,3-hexadiyn-5-yl, 1-octyn-8-yl,1-nonyn-9-yl, 1-decyn-10-yl or 1-tetracosyn-24-yl,

C₄-C₁₈cycloalkyl is preferably C₅-C₁₂cycloalkyl, such as, for example,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl,cyclodecyl, cyclododecyl. Cyclohexyl and cyclododecyl are mostpreferred.

The term “aryl group” is typically C₆-C₃₀aryl, such as phenyl, indenyl,azulenyl, naphthyl, biphenyl, terphenylyl or quadphenylyl, as-indacenyl,s-indacenyl, acenaphthylenyl, phenanthryl, fluoranthenyl, triphenlenyl,chrysenyl, naphthacen, picenyl, perylenyl, pentaphenyl, hexacenyl,pyrenyl, anthracenyl, terphenylyl or quadphenylyl, which can besubstituted or unsubstituted, preferably phenyl, 1-naphthyl, 2-naphthyl,9-phenanthryl, 2- or 9-fluorenyl, 3- or 4-biphenyl, which may beunsubstituted or substituted. Examples of C₆-C₁₈aryl are phenyl,4-methylphenyl, 4-methoxyphenyl, 1-naphthyl, 2-naphthyl, 3- or4-biphenyl, 9-phenanthryl, 2- or 9-fluorenyl, which may be unsubstitutedor substituted.

C₇-C₂₄aralkyl radicals are preferably C₇-C₁₅aralkyl radicals, which maybe substituted, such as, for example, benzyl, 2-benzyl-2-propyl,β-phenethyl, α,α-dimethylbenzyl, ω-phenyl-butyl, ω-phenyl-octyl,ω-phenyl-dodecyl or 3-methyl-5-(1′,1′,3′,3′-tetramethyl-butyl)-benzyl,

The term “heteroaryl group”, especially C₂-C₃₀heteroaryl, is a ring,wherein nitrogen, oxygen or sulfur are the possible hetero atoms, and istypically an unsaturated heterocyclic radical with five to 18 atomshaving at least six conjugated t-electrons such as thienyl,benzo[b]thienyl, dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl,2H-pyranyl, benzofuranyl, isobenzofuranyl, 2H-chromenyl, xanthenyl,dibenzofuranyl, phenoxythienyl, pyrrolyl, imidazolyl, pyrazolyl,pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyrazinyl, 1H-pyrrolizinyl,isoindolyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, 3H-indolyl,phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl,indazolyl, purinyl, quinolizinyl, chinolyl, isochinolyl, phthalazinyl,naphthyridinyl, chinoxalinyl, chinazolinyl, cinnolinyl, pteridinyl,carbazolyl, 4aH-carbazolyl, carbolinyl, benzotriazolyl, benzoxazolyl,phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl,isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl or phenoxazinyl,preferably the above-mentioned mono- or bicyclic heterocyclic radicals,which may be unsubstituted or substituted.

Examples of a five or six membered ring formed by R⁵ and R⁶ and R¹⁰³ andR¹⁰⁴, respectively are heterocycloalkanes or heterocycloalkenes havingfrom 3 to 5 carbon atoms which can have one additional hetero atomselected from nitrogen, oxygen and sulfur, for example

which can be part of a bicyclic system, for example

Possible substituents of the above-mentioned groups are C₁-C₈alkyl, ahydroxyl group, a mercapto group, C₁-C₈alkoxy, C₁-C₈alkylthio, halogen,halo-C₁-C₈alkyl, a cyano group, an aldehyde group, a ketone group, acarboxyl group, an ester group, a carbamoyl group, an amino group, anitro group or a silyl group.

As described above, the aforementioned radicals may be substituted by Eand/or, if desired, interrupted by D. Interruptions are of coursepossible only in the case of radicals containing at least 2 carbon atomsconnected to one another by single bonds; C₆-C₁₈aryl is not interrupted;interrupted arylalkyl or alkylaryl contains the unit D in the alkylmoiety. C₁-C₁₈alkyl substituted by one or more E and/or interrupted byone or more units D is, for example, (CH₂CH₂O)_(n)—R^(x), where n is anumber from the range 1-9 and R^(x) is H or C₁-C₁₀alkyl orC₂-C₁₀alkanoyl (e.g. CO—CH(C₂H₅)C₄H₉), CH₂—CH(OR^(y′))—CH₂—O—R^(y),where R^(y) is C₁-C₁₈alkyl, C₅-C₁₂cycloalkyl, phenyl, C₇-C₁₅phenylalkyl,and R^(y′) embraces the same definitions as R^(y) or is H;

C₁-C₈alkylene-COO—R^(z), e.g. CH₂COOR_(z), CH(CH₃)COOR^(z),C(CH₃)₂COOR^(z), where R^(z) is H, C₁-C₁₈alkyl, (CH₂CH₂O)₁₋₉—R^(x), andR^(x)embraces the definitions indicated above;CH₂CH₂—O—CO—CH═CH₂; CH₂CH(OH)CH₂—O—CO—C(CH₃)═CH₂.

To obtain organic layers of this invention with the proper T_(g), orglass transition temperature, it is advantageous that the presentorganic compounds have a melting point greater than about 150° C., forexample greater than about 200° C., for example greater than about 250°C., for instance greater than about 300° C.

The electroluminescent devices of the present invention are otherwisedesigned as is known in the art, for example as described in U.S. Pat.Nos. 5,518,824, 6,225,467, 6,280,859, 5,629,389, 5,486,406, 5,104,740,5,116,708 and 6,057,048, the relevant disclosures of which are herebyincorporated by reference.

For example, organic EL devices contain one or more layers such as:

substrate; base electrode; hole-injecting layer; hole transportinglayer; emitter layer; electron-transporting layer; electron-injectinglayer; top electrode; contacts and encapsulation.

This structure is a general case and may have additional layers or maybe simplified by omitting layers so that one layer performs a pluralityof tasks. For instance, the simplest organic EL device consists of twoelectrodes which sandwich an organic layer that performs all functions,including the function of light emission.

A preferred EL device comprises in this order:

(a) an anode,(b) a hole injecting layer and/or a hole transporting layer,(c) a light-emitting layer,(d) optionally an electron transporting layer and(e) a cathode.

In particular, the present organic compounds function as light emittersand are contained in the light emission layer or form the light-emittinglayer.

The light emitting compounds of this invention exhibit intensefluorescence in the solid state and have excellentelectric-field-applied light emission characteristics. Further, thelight emitting compounds of this invention are excellent in theinjection of holes from a metal electrode and the transportation ofholes; as well as being excellent in the injection of electrons from ametal electrode and the transportation of electrons. They areeffectively used as light emitting materials and may be used incombination with other hole transporting materials, other electrontransporting materials or other dopants.

The organic compounds of the present invention form uniform thin films.The light emitting layers may therefore be formed of the present organiccompounds alone.

Alternatively, the light-emitting layer may contain a knownlight-emitting material, a known dopant, a known hole transportingmaterial or a known electron transporting material as required. In theorganic EL device, a decrease in the brightness and life caused byquenching can be prevented by forming it as a multi-layered structure.The light-emitting material, a dopant, a hole-injecting material and anelectron-injecting material may be used in combination as required.Further, a dopant can improve the light emission brightness and thelight emission efficiency, and can attain the red or blue lightemission. Further, each of the hole transporting zone, thelight-emitting layer and the electron transporting zone may have thelayer structure of at least two layers. In the hole transporting zone inthis case, a layer to which holes are injected from an electrode iscalled “hole-injecting layer”, and a layer which receives holes from thehole-injecting layer and transport the holes to a light-emitting layeris called “hole transporting layer”. In the electron transporting zone,a layer to which electrons are injected from an electrode is called“electron-injecting layer”, and a layer which receives electrons fromthe electron-injecting layer and transports the electrons to alight-emitting layer is called “electron transporting layer”. Theselayers are selected and used depending upon factors such as the energylevel and heat resistance of materials and adhesion to an organic layeror metal electrode.

The light-emitting material or the dopant which may be used in thelight-emitting layer together with the organic compounds of the presentinvention includes for example anthracene, naphthalene, phenanthrene,pyrene, tetracene, coronene, chrysene, fluorescein, perylene,phthaloperylene, naphthaloperylene, perinone, phthaoperinone,naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarine,oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine,cyclopentadiene, quinoline metal complex, aminoquinoline metal complex,benzoquinoline metal complex, imine, diphenylethylene, vinyl anthracene,diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, animidazole-chelated oxynoid compound, quinacridone, rubrene, andfluorescent dyestuffs for a dyestuff laser or for brightening.

If the pyrimidine compounds of the formula I are used as host, theweight ratio of the pyrimidine compound (host) to the guest compound isin general 50:50 to 99.99:0.01, preferably 90:10 to 99.99:0.01, morepreferably 95:5 to 99.9:0.1 most preferably 98:2 to 99.9:0.1.

The pyrimidine compounds of the present invention and the above compoundor compounds that can be used in a light-emitting layer may be used inany mixing ratio for forming a light-emitting layer. That is, theorganic compounds of the present invention may provide a main componentfor forming a light-emitting layer, or they may be a doping material inanother main material, depending upon a combination of the abovecompounds with the organic compounds of the present invention.

The hole-injecting material is selected from compounds which are capableof transporting holes, are capable of receiving holes from the anode,have an excellent effect of injecting holes to a light-emitting layer ora light-emitting material, prevent the movement of excitons generated ina light-emitting layer to an electron-injecting zone or anelectron-injecting material and have the excellent capability of forminga thin film. Suitable hole-injecting materials include for example aphthalocyanine derivative, a naphthalocyanine derivative, a porphyrinderivative, oxazole, oxadiazole, triazole, imidazole, imidazolone,imidazolthione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole,oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene,butadiene, benzidine type triphenylamine, styrylamine typetriphenylamine, diamine type triphenylamine, derivatives of these, andpolymer materials such as polyvinylcarbazole, polysilane and anelectroconducting polymer.

In the organic EL device of the present invention, the hole-injectingmaterial which is more effective is an aromatic tertiary aminederivative or a phthalocyanine derivative. Although not speciallylimited, specific examples of the tertiary amine derivative includetriphenylamine, tritolylamine, tolyldiphenylamine,N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1-biphenyl-4,4′-diamine,N,N,N′,N′-tetra(4-methylphenyl)-1,1′-phenyl-4,4′-diamine,N,N,N′,N′-tetra(4-methylphenyl)-1,1′-biphenyl-4,4′-diamine,N,N′-diphenyl-N,N′-di(1-naphthyl)-1,1′-biphenyl-4,4′-diamine,N,N′-di(methylphenyl)-N,N′-di(4-n-butylphenyl)-phenanthrene-9,10-diamine,4,4′, 4″-tris(3-methylphenyl)-N-phenylamino)triphenylamine,1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, and oligomers or polymershaving aromatic tertiary amine structures of these.

Although not specially limited, specific examples of the phthalocyanine(Pc) derivative include phthalocyanine derivatives or naphthalocyaninederivatives such as H₂Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc,ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl₂SiPc, (HO)AlPc, (HO)GaPc, VOPc,TiOPc, MoOPc, and GaPc-O-GaPc.

The hole transporting layer can reduce the driving voltage of the deviceand improve the confinement of the injected charge recombination withinthe pyrimidin light emitting layer. Any conventional suitable aromaticamine hole transporting materials described for the hole-injecting layermay be selected for forming this layer.

A preferred class of hole transporting materials is comprised of4,4′-bis(9-carbazolyl)-1,1′-biphenyl compounds of the formula

wherein R⁶¹ and R⁶² is a hydrogen atom or an C₁-C₃alkyl group; R⁶³through R⁶⁶ are substituents independently selected from the groupconsisting of hydrogen, a C₁-C₆alkyl group, a C₁-C₆alkoxy group, ahalogen atom, a dialkylamino group, a C₆-C₃₀aryl group, and the like.Illustrative examples of 4,4′-bis(9-carbazolyl)-1,1′-biphenyl compoundsinclude 4,4′-bis(9-carbazolyl)-1,1′-biphenyl and4,4′-bis(3-methyl-9-carbazolyl)-1,1′-biphenyl, and the like.

The electron transporting layer is not necessarily required for thepresent device, but is optionally and preferably used for the primarypurpose of improving the electron injection characteristics of the ELdevices and the emission uniformity. Illustrative examples of electrontransporting compounds, which can be utilized in this layer, include themetal chelates of 8-hydroxyquinoline as disclosed in U.S. Pat. Nos.4,539,507, 5,151,629, and 5,150,006, the disclosures of which aretotally incorporated herein by reference.

Although not specially limited, specific examples of the metal complexcompound include lithium 8-hydroxyquinolinate, zincbis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganesebis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminumtris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate),beryllium bis(10-hydroxybenzo[h]quinolinate), zincbis(10-hydroxybenzo[h]quinolinate), chlorogalliumbis(2-methyl-8-quinolinate), galliumbis(2-methyl-8-quinolinate)(o-cresolate), aluminumbis(2-methyl-8-quinolinate)(1-naphtholate), galliumbis(2-methyl-8-quinolinate)(2-naphtholate), galliumbis(2-methyl-8-quinolinate)phenolate, zincbis(o-(2-benzooxazolyl)phenolate), zincbis(o-(2-benzothiazolyl)phenolate) and zincbis(o-(2-benzotrizolyl)phenolate). The nitrogen-containing five-memberedderivative is preferably an oxazole, thiazole, thiadiazole, or triazolederivative.

Although not specially limited, specific examples of the abovenitrogen-containing five-membered derivative include2,5-bis(1-phenyl)-1,3,4-oxazole,1,4-bis(2-(4-methyl-5-phenyloxazolyl)benzene,2,5-bis(1-phenyl)-1,3,4-thiazole, 2,5-bis(1-phenyl)-1,3,4-oxadiazole,2-(4′-tert-butylphenyl)-5-(4″-biphenyl)1,3,4-oxadiazole,2,5-bis(1-naphthyl)-1,3,4-oxadiazole,1,4-bis[2-(5-phenyloxadiazolyl)]benzene,1,4-bis[2-(5-phenyloxadiazolyl)-4-tert-butylbenzene],2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-thiadiazole,2,5-bis(1-naphthyl)-1,3,4-thiadiazole,1,4-bis[2-(5-phenylthiazolyl)]benzene,2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-triazole,2,5-bis(1-naphthyl)-1,3,4-triazole and1,4-bis[2-(5-phenyltriazolyl)]benzene. Another class of electrontransport materials are oxadiazole metal chelates, such asbis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-oxadiazolato]beryllium;bis[5-biphenyl-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]zinc;bis[5-biphenyl-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]beryllium;bis(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]lithium;bis[2-(2-hydroxyphenyl)-5-p-tolyl-1,3,4-oxadiazolato]zinc; bis2-(2-hydroxyphenyl)-5-p-tolyl-1,3,4-oxadiazolato]beryllium;bis[5-(p-tert-butylphenyl)-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]zinc;bis[5-(p-tert-butylphenyl)-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(3-fluorophenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(4-fluorophenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(4-fluorophenyl)-1,3,4-oxadiazolato]beryllium;bis[5-(4-chlorophenyl)-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxy phenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxy-4-methylphenyl)-5-phenyl-1,3,4-oxadiazolato]zinc;bis[2-.alpha.-(2-hydroxynaphthyl)-5-phenyl-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-p-pyridyl-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-p-pyridyl-1,3,4-oxadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(2-thiophenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-thiadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-thiadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-thiadiazolato]zinc; andbis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-thiadiazolato]beryllium,and the like.

In the organic EL device of the present invention, the light-emittinglayer may contain, in addition to the light-emitting organic material ofthe present invention, at least one of other light-emitting material,other dopant, other hole-injecting material and other electron-injectingmaterial. For improving the organic EL device of the present inventionin the stability against temperature, humidity and ambient atmosphere, aprotective layer may be formed on the surface of the device, or thedevice as a whole may be sealed with a silicone oil, or the like.

The electrically conductive material used for the anode of the organicEL device is suitably selected from those materials having a workfunction of greater than 4 eV. The electrically conductive materialincludes carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten,silver, gold, platinum, palladium, alloys of these, metal oxides such astin oxide and indium oxide used for ITO substrates or NESA substrates,and organic electroconducting polymers such as polythiophene andpolypyrrole.

The electrically conductive material used for the cathode is suitablyselected from those having a work function of smaller than 4 eV. Theelectrically conductive material includes magnesium, calcium, tin, lead,titanium, yttrium, lithium, ruthenium, manganese, aluminum and alloys ofthese, while the electrically conductive material shall not be limitedto these. Examples of the alloys include magnesium/silver,magnesium/indium and lithium/aluminum, while the alloys shall not belimited to these. Each of the anode and the cathode may have a layerstructure formed of two layers or more as required.

For the effective light emission of the organic EL device, at least oneof the electrodes is desirably sufficiently transparent in the lightemission wavelength region of the device. Further, the substrate isdesirably transparent as well. The transparent electrode is producedfrom the above electrically conductive material by a deposition methodor a sputtering method such that a predetermined light transmittance issecured. The electrode on the light emission surface side has forinstance a light transmittance of at least 10%. The substrate is notspecially limited so long as it has adequate mechanical and thermalstrength and has transparency. For example, it is selected from glasssubstrates and substrates of transparent resins such as a polyethylenesubstrate, a polyethylene terephthalate substrate, a polyether sulfonesubstrate and a polypropylene substrate.

In the organic EL device of the present invention, each layer can beformed by any one of dry film forming methods such as a vacuumdeposition method, a sputtering method, a plasma method and an ionplating method and wet film forming methods such as a spin coatingmethod, a dipping method and a flow coating method. The thickness ofeach layer is not specially limited, while each layer is required tohave a proper thickness. When the layer thickness is too large,inefficiently, a high voltage is required to achieve predeterminedemission of light. When the layer thickness is too small, the layer isliable to have a pinhole, etc., so that sufficient light emissionbrightness is hard to obtain when an electric field is applied. Thethickness of each layer is for example in the range of from about 5 nmto about 10 μm, for instance about 10 nm to about 0.2 μm.

In the wet film forming method, a material for forming an intended layeris dissolved or dispersed in a proper solvent such as ethanol,chloroform, tetrahydrofuran and dioxane, and a thin film is formed fromthe solution or dispersion. The solvent shall not be limited to theabove solvents. For improving the film formability and preventing theoccurrence of pinholes in any layer, the above solution or dispersionfor forming the layer may contain a proper resin and a proper additive.The resin that can be used includes insulating resins such aspolystyrene, polycarbonate, polyarylate, polyester, polyamide,polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylateand cellulose, copolymers of these, photoconductive resins such aspoly-N-vinylcarbozole and polysilane, and electroconducting polymerssuch as polythiophene and polypyrrole. The above additive includes anantioxidant, an ultraviolet absorbent and a plasticizer.

When the light-emitting organic material of the present invention isused in a light-emitting layer of an organic EL device, an organic ELdevice can be improved in organic EL device characteristics such aslight emission efficiency and maximum light emission brightness.Further, the organic EL device of the present invention is remarkablystable against heat and electric current and gives a usable lightemission brightness at a low actuation voltage. The problematicdeterioration of conventional devices can be remarkably decreased.

The organic EL device of the present invention has significantindustrial values since it can be adapted for a flat panel display of anon-wall television set, a flat light-emitting device, a light source fora copying machine or a printer, a light source for a liquid crystaldisplay or counter, a display signboard and a signal light.

The material of the present invention can be used in the fields of anorganic EL device, an electrophotographic photoreceptor, a photoelectricconverter, a solar cell, an image sensor, dye lasers and the like.

The following Examples illustrate the invention. In the Examples andthroughout this application, the term light emitting material means thepresent pyrimidine compounds.

EXAMPLES Example 1 (A-1)

To 1.00 g (2.69 mmol) of educt 1 (prepared according to U.S. Pat. No.3,442,898 from resorcinol and 4,6-dichloro-2-phenyl-pyrimidine; J. Org.Chem. 1988, 53, 4137) in 20 ml water free DMF 3.29 g (21.5 mmol)methyl-bromoacetate and 2.97 g (21.5 mmol) potassium carbonate areadded. The reaction mixture is stirred at 100° C. under nitrogen for 2h. The reaction mixture is diluted with water. The organic phase isextracted with dichloromethane und dried with magnesium sulfate. Thesolvent is removed. After chromatography of the crude product on silicagel with toluene/ethyl acetate 8/2 the desired product is obtained.Melting point: 178.0-179.0° C.

Example 2 (A-2)

To 520 mg (1.16 mmol) of educt 2 (prepared according to U.S. Pat. No.3,442,898 from resorcinol and 4,6-dichloro-2-biphenyl-pyrimidine;EP-A-96657) in 20 ml water free DMF 1.42 g (9.28 mmol)methyl-bromoacetate and 1.28 g (9.28 mmol) potassium carbonate areadded. The reaction mixture is stirred at 100° C. under nitrogen for 2h. The reaction mixture is diluted with water. The organic phase isextracted with dichloromethane und dried with magnesium sulfate. Thesolvent is removed. After chromatography of the crude product on silicagel with toluene/ethyl acetate 9/1 and later 7/3 the desired product isobtained. Melting point: 119.5-121.5° C.

Example 3 (A-3)

To 4.31 g (16.1 mmol) of 1,3-bis(4-methoxyphenyl)-2-propen-1-one in 25ml water free ethanol 1.89 g (8.11 mmol) biphenylbenzamidinehydrochlorid are added. A solution of 1.07 g (19.08 mmol) potassiumhydroxide is added during 15 min. Dry air is bubbled through thereaction mixture. The reaction mixture is refluxed for 24 h. Thereaction mixture is poured into water. The solid is filtered off andwashed with water. The product is crystallized 2 times from acetic acid(96-98%). Melting point: 168-169° C.

Compounds A-4 to A-54 can be obtained in a manner analogous to Examples1 to 5.

(A-54; melting point: 162-164° C.)

Cpd. X³ Y³ W³ X⁵ Y¹ W⁵ V A-1 H OCH₂COOMe OCH₂COOMe H OCH₂COOMe OCH₂COOMeH A-2 Ph OCH₂COOMe OCH₂COOMe H OCH₂COOMe OCH₂COOMe H A-3 H OMe OMe H H HH A-4¹⁾ H Ph Ph H H H H A-5 H OMe OMe H OMe OMe H A-6 H OBu OBu H H H HA-7 H OBu OBu H OBu OBu H A-8 OMe OMe OMe OMe OMe OMe H A-9 OMe Br BrOMe H H H A-10 Ph Br Br H H H H A-11 OMe Ph Ph OMe H H H A-12 Ph Ph Ph HH H H A-13 SMe SMe SMe H H H H A-14 H SMe SMe H H H H A-15 H OCH₂CH₂OAcOCH₂CH₂OAc H H H H A-16 H OCH₂CH₂OAc OCH₂CH₂OAc H OCH₂CH₂OAc OCH₂CH₂OAcH A-17 H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et H H H H A-18 H OCH₂CH₂OCH₂EtOCH₂CH₂OCH₂Et H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et H A-19 H N(CH₃)₂ N(CH₃)₂ H HH H A-20 H

H H H H A-21 Ph N(CH₃)₂ N(CH₃)₂ H H H H A-22 Ph

H H H H A-23 H CH₃ CH₃ H H H H A-24 Ph CH₃ CH₃ H H H H A-25 Ph Ph Ph H HH CH₃ A-26 OMe OMe OMe H H H CH₃ A-27 H Ph Ph H H H CH₃ ¹⁾melting point:244-245° C.

Cpd. X³ Y³ W³ X⁵ Y¹ W⁵ V A-28 H OMe OMe H H H CH₃ A-29 H OMe OMe H OMeOMe CH₃ A-30 H OBu OBu H H H CH₃ A-31 H OBu OBu H OBu OBu CH₃ A-32 OMeOMe OMe OMe OMe OMe CH₃ A-33 OMe Br Br OMe H H CH₃ A-34 Ph Br Br H H HCH₃ A-35 OMe Ph Ph OMe H H CH₃ A-36 H OCH₂COOMe OCH₂COOMe H OCH₂COOMeOCH₂COOMe CH₃ A-37 SMe SMe SMe H H H CH₃ A-38 H SMe SMe H H H CH₃ A-39 HOCH₂CH₂Oac OCH₂CH₂Oac H H H CH₃ A-40 H OCH₂CH₂Oac OCH₂CH₂Oac HOCH₂CH₂Oac OCH₂CH₂Oac CH₃ A-41 H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et H H H CH₃A-42 H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et CH₃A-43 OBu Ph Ph OBu H H CH₃ A-44 H N(CH₃)₂ N(CH₃)₂ H H H CH₃ A-45 H

H H H CH₃ A-46 Ph N(CH₃)₂ N(CH₃)₂ H H H CH₃ A-47 Ph

H H H CH₃ A-48 Ph CH₃ CH₃ H H H CH₃ A-49 Ph CH₃ CH₃ H H H CH₃ A-50 OMeOMe OMe H H H H A-51¹⁾ H H H H H H H A-52²⁾ Ph H H H H H H ¹⁾meltingpoint: 188-189° C. ²⁾melting point: 196-198° C.

Example 4 (B-1)

To 5.00 g (16.1 mmol) of 1,3-bis-α-naphthy-2-propen-1-one (1) in 25 mlwater free ethanol 1.89 g (8.11 mmol) biphenylbenzamidine hydrochloridare added. A solution of 1.07 g (19.08 mmol) potassium hydroxide in 25ml water free ethanol is added during 15 min. Dry air was bubbledthrough the reaction mixture. The reaction mixture is refluxed for 24 h.

The reaction mixture is poured into water. The solid is filtered off andis washed with water.

The product is crystallized 2 times from acetic acid (96-98%). Meltingpoint: 226-230° C.

Example 5 (B-2)

To 5.00 g (16.1 mmol) of 1,3-bis-α-naphthy-2-propen-1-one (1) in 25 mlwater free ethanol 1.27 g (8.11 mmol) benzamidine hydrochlorid areadded. A solution of 1.07 g (19.08 mmol) potassium hydroxide in 25 mlwater free ethanol is added during 15 min. Dry air is bubbled throughthe reaction mixture. The reaction mixture is refluxed for 24 h. Thereaction mixture is poured into water. The solid is filtered off and iswashed with water. The product is crystallized from acetic acid(96-98%). Melting point: 179-180° C.

Compounds B-3 to B-23 can be obtained in a manner analogous to Examples4 and 5.

Cpd. X³ Y³ W³ X⁵ V B-1 Ph H H H H B-2 H H H H H B-3 OBu H H OBu H B-4OMe H H OMe H B-5 OCH₂COOMe H H OCH₂COOMe H B-6 H OMe OMe H H B-7OCH₂CH₂OCH₂Et H H OCH₂CH₂OCH₂Et H B-8 OCH₂CH₂OAc H H OCH₂CH₂OAc H B-9OMe OMe OMe OMe H B-10 OMe OMe OMe OMe H B-11 H CH₃ CH₃ H H B-12 Ph CH₃CH₃ H H B-13 Ph H H H CH₃ B-14 OMe H H OMe CH₃ B-15 OBu H H OBu CH₃ B-16H H H H CH₃ B-17 OCH₂COOMe H H OCH₂COOMe CH₃ B-18 H OMe OMe H CH₃ B-19OCH₂CH₂OCH₂Et H H OCH₂CH₂OCH₂Et CH₃ B-20 OCH₂CH₂OAc H H OCH₂CH₂OAc CH₃B-21 H CH₃ CH₃ H CH₃ B-22 Ph CH₃ CH₃ H CH₃

Example 6 (C-1)

To 4.50 g (8.74 mmol) of the 2-propen-1-one derivative shown above in 50ml water free ethanol 1.37 g (8.74 mmol) benzamidine hydrochloride areadded. A solution of 1.15 g (20.6 mmol) potassium hydroxide in 50 mlwater free ethanol is added during 15 min. Dry air is bubbled throughthe reaction mixture. The reaction mixture is refluxed for 24 h, pouredinto water and the water phase is extracted with dichloromethane. Theorganic phase is dried with magnesium sulfate, the solvent is removed bydistillation and the remaining residue is purified by columnchromatography (toluene/hexane 2/1).

¹H-NMR (300 MHz, CDCl₃): δ=8.75-8.72 (m, 4H); 8.45-8.37 (m, 12H);8.04-7.82 (m, 6H); 7.67-7.50 (m, 12h).

Compounds C-2 to C-24 can be obtained in a manner analogous to Example6.

Cpd. W³ Y³ C-2 H H C-3 H H C-4 H H C-5 H H C-6 H H C-7 OCH₃ OCH₃ C-8OCH₃ OCH₃ C-9 OCH₃ OCH₃ C-10 OCH₃ OCH₃ C-11 OCH₃ OCH₃ C-12 SCH₃ SCH₃C-13 SCH₃ SCH₃ C-14 SCH₃ SCH₃ C-15 SCH₃ SCH₃ C-16 SCH₃ SCH₃ C-17 SCH₃SCH₃ C-18 N(CH₃)₂ N(CH₃)₂ C-19 N(CH₃)₂ N(CH₃)₂ C-20 N(CH₃)₂ N(CH₃)₂ C-21N(CH₃)₂ N(CH₃)₂ C-22 N(CH₃)₂ N(CH₃)₂ C-23 N(CH₃)₂ N(CH₃)₂ C-24 N(CH₃)₂N(CH₃₎₂

Compounds D-1 to D-23 can be obtained in a manner analogous to Example6.

Cpd. R¹⁰¹ R¹⁰² W³ Y³ D-1 C₆H₁₃ C₆H₁₃ H H D-2 Bu Bu H H D-3 Et Et H H D-4H H H H D-5 Ph Ph H H D-6 C₆H₁₃ C₆H₁₃ OCH₃ OCH₃ D-7 Bu Bu OCH₃ OCH₃ D-8Et Et OCH₃ OCH₃ D-9 H H OCH₃ OCH₃ D-10 Ph Ph OCH₃ OCH₃ D-11 C₆H₁₃ C₆H₁₃SCH₃ SCH₃ D-12 Bu Bu SCH₃ SCH₃ D-13 Et Et SCH₃ SCH₃ D-14 H H SCH₃ SCH₃D-15 Ph Ph SCH₃ SCH₃ D-16 C₆H₁₃ C₆H₁₃ SCH₃ SCH₃ D-17 C₆H₁₃ C₆H₁₃ N(CH₃)₂N(CH₃)₂ D-18 Bu Bu N(CH₃)₂ N(CH₃)₂ D-19 Et Et N(CH₃)₂ N(CH₃)₂ D-20 H HN(CH₃)₂ N(CH₃)₂ D-21 Ph Ph N(CH₃)₂ N(CH₃)₂ D-22 C₆H₁₃ C₆H₁₃ N(CH₃)₂N(CH₃)₂ D-23 Bu Bu N(CH₃)₂ N(CH₃)₂Compounds E-1 to E-35 can be obtained in a manner analogous to Example6.

Cpd. Y³ X³ E-1 H H E-2 H H E-3 H H E-4 H H E-5 H H E-6 OCH₃ OCH₃ E-7OCH₃ OCH₃ E-8 OCH₃ OCH₃ E-9 OCH₃ OCH₃ E-10 OCH₃ OCH₃ E-11 OCH₃ H E-12OCH₃ H E-13 OCH₃ H E-14 OCH₃ H E-15 OCH₃ H E-16 SCH₃ SCH₃ E-17 SCH₃ SCH₃E-18 SCH₃ SCH₃ E-19 SCH₃ SCH₃ E-20 SCH₃ SCH₃ E-21 SCH₃ H E-22 SCH₃ HE-23 SCH₃ H E-24 SCH₃ H E-25 SCH₃ H E-26 N(CH₃)₂ N(CH₃)₂ E-27 N(CH₃)₂N(CH₃)₂ E-28 N(CH₃)₂ N(CH₃)₂ E-29 N(CH₃)₂ N(CH₃)₂ E-30 N(CH₃)₂ N(CH₃)₂E-31 N(CH₃)₂ H E-32 N(CH₃)₂ H E-33 N(CH₃)₂ H E-34 N(CH₃)₂ H E-35 N(CH₃)₂H

Compounds F-1 to F-35 can be obtained in a manner analogous to Example6.

Cpd. R¹⁰¹ R¹⁰² Y³ X³ F-1 C₆H₁₃ C₆H₁₃ H H F-2 Bu Bu H H F-3 Et Et H H F-4H H H H F-5 Ph Ph H H F-6 C₆H₁₃ C₆H₁₃ OCH₃ OCH₃ F-7 Bu Bu OCH₃ OCH₃ F-8Et Et OCH₃ OCH₃ F-9 H H OCH₃ OCH₃ F-10 Ph Ph OCH₃ OCH₃ F-11 C₆H₁₃ C₆H₁₃OCH₃ H F-12 Bu Bu OCH₃ H F-13 Et Et OCH₃ H F-14 H H OCH₃ H F-15 Ph PhOCH₃ H F-16 C₆H₁₃ C₆H₁₃ SCH₃ SCH₃ F-17 Bu Bu SCH₃ SCH₃ F-18 Et Et SCH₃SCH₃ F-19 H H SCH₃ SCH₃ F-20 Ph Ph SCH₃ SCH₃ F-21 C₆H₁₃ C₆H₁₃ SCH₃ HF-22 Bu Bu SCH₃ H F-23 Et Et SCH₃ H F-24 H H SCH₃ H F-25 Ph Ph SCH₃ HF-26 C₆H₁₃ C₆H₁₃ N(CH₃)₂ N(CH₃)₂ F-27 Bu Bu N(CH₃)₂ N(CH₃)₂ F-28 Et EtN(CH₃)₂ N(CH₃)₂ F-29 H H N(CH₃)₂ N(CH₃)₂ F-30 Ph Ph N(CH₃)₂ N(CH₃)₂ F-31C₆H₁₃ C₆H₁₃ N(CH₃)₂ H F-32 Bu Bu N(CH₃)₂ H F-33 Et Et N(CH₃)₂ H F-34 H HN(CH₃)₂ H F-35 Ph Ph N(CH₃)₂ H

Example 7 (G-1)

To 14.6 g (0.100 mol) of tetralone and 15.0 g (1.10 mol)p-methoxy-benzaldehyd in 100 ml absolute methanol 660 mg potassiumhydroxide are added. The reaction mixture is refluxed for 18 h underargon and then cooled to 25° C. The formed product is filtered off andwashed with methanol. To 6.61 g (25.0 mmol) of said product in 50 mlwater free ethanol 1.96 g (12.5 mmol) benzamidine hydrochloride areadded. A solution of 1.65 g (25.0 mmol) potassium hydroxide in 50 mlwater free ethanol is added during 15 min. Dry air is bubbled throughthe reaction mixture. The reaction mixture is refluxed for 24 h and thenpoured into water. The water phase is extracted with dichloromethane.The organic phase is dried with magnesium sulfate, the solvent isremoved by distillation and the remaining residue is purified by columnchromatography (toluene/hexane 1/1). The product G-1 having a meltingpoint of 169° C. is obtained.

Example 8 (H-1)

a) 24.9 g (0.134 mol) 4-bromo-benzaldehyde and 26.8 g4-bromo-acetophenone (0.134 mol) are dissolved under argon in 120 mlmethanol. To this solution 0.270 g sodium hydroxide are added. Thereaction mixture is stirred for 5 h. The formed yellow product isfiltered off and is washed with water and then methanol. The product isdried in a vacuum oven (yield: 44.2 g (90%), melting point: 183-184°C.).

b) To 5.00 g (13.7 mmol) of 1,3-bis-(4-bromophenyl)-2-propen-1-one (1)in 25 ml water free ethanol 1.61 g (6.83 mmol) 4-bromo-benzamidinehydrochloride are added under argon. A solution of 0.90 g (16.1 mmol)potassium hydroxide in 25 ml water free ethanol is added during 15 min.Dry air is bubbled through the reaction mixture. The reaction mixture isrefluxed for 24 h and then poured into water. The product is filteredoff, washed with ethanol and dried in a vacuum oven (melting point:321-322° C.).

c) To 1.00 g (1.83 mmol) of tris-2,4,6-(4-bromo-phenyl)-pyrimidine and1.27 g (6.42 mmol) of 4-biphenylboronic acid in 20 ml toluene 5.27 g(16.19 mmol) CsCO₃ in 3 ml water are added under argon. Approximately 10mg of the Pd catalyst (WO 99/47474) are added and then the reactionmixture is refluxed for 5 h. The product is filtered off, washed withwater and acetone. The product is dissolved in dichloromethane andfiltered on silica gel. The solvent is removed in vacuum. The obtainedproduct has a melting point of 364-367° C.

Example 9 (H-2)

a) The product (melting point: 204-205° C.) is prepared according to theprocedure given in example 8b).

b) The product (melting point: 343-345° C.) is prepared according to theprocedure given in example 8c).

Example 10 (H-3)

a) The product (melting point: 207-208° C.) is prepared according to theprocedure given in example 8b).

b) The product (melting point: 364-367° C.) is prepared according to theprocedure given in example 8c).

Example 11 (H-4)

a) The product (melting point: 145-146° C.) is prepared according to theprocedure given in example 8b) (yield: 86%).

b) The product (melting point: 160° C.) is prepared according to theprocedure given in example 8b) (yield: 72%).

c) The product (melting point: 213-214° C.) is prepared according to theprocedure given in example 8c) (yield: 53%).

Example 12 (H-5)

a) The product (melting point: 122-123° C.) is prepared according to theprocedure given in example 8b) (yield: 91%).

b) The product (melting point: 152-153° C.) is prepared according to theprocedure given in example 8b) (yield: 54%).

c) The product (melting point: 220-221° C.) is prepared according to theprocedure given in example 8c) (yield: 80%).

Example 13 (H-6)

a) The product (melting point: 245-246° C.) is prepared according to theprocedure given in example 8b) (yield: 42%).

b) The product (melting point: 333-334° C.) is prepared according to theprocedure given in example 8c) (yield: 75%).

Example 14 (H-7)

a) The product (melting point: 204-205° C.) is prepared according to theprocedure given in example 8b) (yield: 46%).

b) The product (melting point: 329-331° C.) is prepared according to theprocedure given in example 8c) (yield: 61%).

Example 15

To 264 mg (1.0 mmol) of the pyrimidine (see scheme above) in 20 mlchloroform 454 mg (2.0 mmol) DDQ are added. The reaction mixture isrefluxed for 1 day. Additional 908 mg (4.0 mmol) of DDQ are added andthe reaction mixture is refluxed for additional 2 days. The reactionmixture is filtered on silica gel with dichloromethane. A columnchromatography on silica gel with toluene gives the desired product in61% yield (mp. 163-165° C.).

Example 16 (J-1)

a) 10.0 g (57.2 mol) 3,4-dimethoxy-benzaldehyde and 10.3 g (57.2 mol)3,4-dimethoxy-acetophenone are dissolved under argon in 50 ml methanol.To this solution 0.34 g sodium hydroxide are added. The reaction mixtureis stirred for 22 h at 40° C. The reaction mixture is cooled to 0° C.and the precipitated product is filtered off. The product is dried invacuum (yield: 18.2 g (97%), melting point: 108-110° C.).

b) To 7.00 g (21.3 mmol) of1,3-bis-(3,4-dimethoxy-phenyl)-2-propen-1-one (1) in 40 ml water freeethanol 1.67 g (10.7 mmol) benzamidine hydrochloride are added underargon. A solution of 1.41 g (25.1 mmol) potassium hydroxide (85%) in 40ml water free ethanol is added during 20 min. Dry air is bubbled throughthe reaction mixture. The reaction mixture is refluxed for 48 h and thenpoured into water. The product is filtered off and washed with ethanol.A column chromatography on silica gel with toluene gives the desiredproduct J-1 (melting point: 157-158° C.).

Example 17 (J-2)

a) 10.0 g (57.2 mol) 2,4-dimethoxy-benzaldehyde and 10.3 g2,4-dimethoxy-acetophenone (57.2 mol) are dissolved under argon in 50 mlmethanol. To this solution 0.34 g sodium hydroxide are added. Thereaction mixture is stirred for 48 h at 40° C. The reaction mixture isdiluted with water and the precipitated product is filtered off. Theproduct is washed with water and dried in vacuum (melting point:127-129° C.).

b) To 6.60 g (20.1 mmol) of1,3-bis-(2,4-dimethoxy-phenyl)-2-propen-1-one (1) in 40 ml water freeethanol 2.34 g (10.1 mmol) biphnenyl-benzamidine hydrochloride are addedunder argon. A solution of 1.41 g (25.1 mmol) potassium hydroxide (85%)in 40 ml water free ethanol is added during 15 min. Dry air is bubbledthrough the reaction mixture. The reaction mixture is refluxed for 48 hand then poured into water. The water phase is extracted withdichloromethane. The organic phase is dried with MgSO₄ and the solventis removed in vacuum. A column chromatography on silica gel withtoluene/hexane 3/2 give the desired product J-2 (melting point: 165-167°C.).

Example 18 (J-4)

To 5.50 g (15.2 mmol) of 1,3-bis-(2,4-dimethoxy-phenyl)-2-propen-1-one(1) in 30 ml water free ethanol 0.87 g (9.14 mmol) guanidinehydrochloride are added under argon. A solution of 1.21 g (21.5 mmol)potassium hydroxide (85%) in 30 ml water free ethanol is added during 15min. Dry air is bubbled through the reaction mixture. The reactionmixture is refluxed for 48 h and then poured into water. The water phaseis extracted with dichloromethane. The organic phase is dried with MgSO₄and the solvent is removed in vacuum. A column chromatography on silicagel with dichloromethane/ethyl acetate 2/1 gives the desired product(melting point: 211-213° C.).

Example 19 (J-5)

a) To a suspension of 0.69 g sodium hydride in 25 ml terahydrofurane(THF) 5.38 g (27.4 mmol) 4-acetyl-biphenyl are added at 0° C. underargon. After 1 h 5.00 g (27.4 mmol) 4-bihenylcarbadehyde in 25 ml THFare added. The reaction mixture is stirred for 19 h at 25° C. The formedprecipitate is filtered off and washed with THF. The product is refluxedfor 1 h in 100 ml iso-propanol and 30 ml water. The product is filteredoff and dried in vacuum.

b) The desired product J-5 (melting point: 245-246° C.) is preparedaccording to the procedure given in example 17b).

Example 20 (J-6)

The product J-6 (melting point: 243-246° C.) is prepared according tothe procedure given in example 17b).

Example 21 (J-7)

a) 18.3 g (0.100 mol) 2,4-dimethoxy-benzaldehyde and 12.1 g (0.100 mol)3-acethyl pyridine are dissolved under argon in 100 ml methanol. To thissolution 0.66 g sodium hydroxide are added. The reaction mixture isrefluxed for 18 h. The reaction mixture is poured into water andextracted with dichloromethane. The organic phase is dried with MgSO₄and the solvent is removed in vacuum. A column chromatography on silicagel with toluene/ethyl acetate 2/1 give the desired product (yield: 7.3g (27%)).

b) The product J-7 (melting point: 136° C.) is prepared according to theprocedure given in example 17b).

Example 22 (K-1)

a) To 10.0 g (27.3 mmol) of 1,3-bis-(4-bromophenyl)-2-propen-1-one in 70ml ethanol 2.14 g (13.7 mmol) benzamidine hydrochloride are added underargon. A solution of 1.80 g (32.1 mmol) potassium hydroxide (85%) in 50ml ethanol is added during 15 min. Dry air is bubbled through thereaction mixture. The reaction mixture is refluxed for 24 h and then ispoured into water. The product is filtered off, washed with water and10% tartaric acid, crystallized from glacial acetic acid and washed withethanol (yield: 9.2 g (58%); melting point: 203-205° C.).

b) To 4.45 g (9.55 mmol) 4,6-tris-(p-bromophenyl)-2-phenyl-pyrimidine in200 ml toluene 2.99 g (19.1 mmol) 4-chloro-phenylboronic acid are added.The suspension is refluxed under argon. Argon is passed through thereaction mixture. 9.33 g (28.6 mmol) of caesium carbonate in 6 ml waterare added dropwise to the reaction mixture. Then 0.40 g of the catalystare added. The reaction mixture is refluxed for 16 h and then the solidsare filtered off. The solvent is removed in vacuum. The residue isdissolved in dichloromethane and is washed with water. The organic phaseis dried with magnesium sulfate. The solvent is removed in vacuum. Theproduct is crystallized from 100 ml ethanol (yield: 99%; melting point:258-259° C.).

c) To 1.00 g (1.89 mmol) 4,6-bis-(p-bromophenyl)-2-phenyl-pyrimidine in45 ml toluene 287 mg (1.89 mmol) 4-metoxy-biphenylboronic acid areadded. Argon is passed through the reaction mixture. 1.23 g (3.78 mmol)of caesium carbonate in 6 ml water is added dropwise to the reactionmixture. Then 20 mg of the catalyst is added. The reaction mixture isrefluxed for 18 h. Additional 4-methoxy-biphenylboronic acid and caesiumcarbonate is added in a 1 to 1 molar ratio until the reaction iscomplete. The product is filtered off and is washed with ethanol, waterand again ethanol. The product is dissolved in boiling DMF, filtered onsuper gel (Fluka 56678, CAS [91053-39-3]) and crystallized (yield: 0.90g (71%); melting point: 345-348° C.).

In a manner analogous to Example 22 Compounds K-2 to K-15 are obtained.

Cpd. Ar K-1

K-2

K-3

K-4

K-5

K-6

K-7

K-8

K-9

K-10

K-11

K-12

K-13

K-14

K-15

K-16

Example 23 (L-1)

a) The product is prepared according to the procedure given in example22a).

b) The product is prepared according to the procedure given in example22b).

c) The product is prepared according to the procedure given in example22c).

In a manner analogous to Example 23 Compounds L-2 to L-15 are obtained.

Cpd. Ar L-1

L-2

L-3

L-4

L-5

L-6

L-7

L-8

L-9

L-10

L-11

L-12

L-13

L-14

L-15

L-16¹⁾

¹⁾A 100 nm thin film of Compound L-16 showed good film quality andstrong photoluminescence at 430 nm (λ_(max)).

Example 24 (M-1)

a) The product is prepared according to the procedure given in example22b).

b) The product is prepared according to the procedure given in example22c).

In a manner analogous to Example 24 Compounds M-2 to M-15 are obtained.

Cpd. Ar M-1

M-2

M-3

M-4

M-5

M-6

M-7

M-8

M-9

M-10

M-11

M-12

M-13

M-14

M-15

M-16

Example 25 (N-1)

1.0 g (1.83 mmol) 2,4,6-tris-(p-bromophenyl)-pyrimidine, 1.49 g (8.26mmol) 1,1-diphenylethylen, 40 mg Palladium-(II)-acetate, 150 mg (1.47mmol) dimethylglycine, 1.39 g (16.5 mmol) sodium hydrogen carbonate and70 mg (0.46 mmol) FeCl₃ are dissolved in 8 ml N-methyl-pyrrolidone. Thereaction mixture is heated for 48 h at 150° C. The reaction mixture ispoured into water and 20% hydrochloric acid is added. The water phase isextracted with dichloromethane. The organic phase is dried withmagnesium sulfate. The solvent is distilled off. A column chromatography(silica gel, toluene/hexane 1/3) result in the desired product(119.5-120.5° C.).

Example 26

The product is synthesized as described in Example 31 of CH-A-542212.

Application Example 1

Present compounds A1, A2, A3, B1, B2, C1, G1 and H1 as light emittingmaterials, respectively, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole and apolycarbonate resin in a weight ratio of 5:3:2 are dissolved intetrahydrofuran, and the solution is spin-coated on a cleaned glasssubstrate with an ITO electrode to form a light-emitting layer having athickness of 100 nm. An electrode having a thickness of 150 nm is formedthereon from a magnesium/indium alloy having a magnesium/indium mixingratio of 10/1, to obtain an organic EL device. The device exhibits lightemission with excellent brightness and efficiency at a direct currentvoltage of 5 V.

Application Example 2

Compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, arevacuum-deposited on a cleaned glass substrate with an ITO electrode toform a light-emitting layer having a thickness of 100 nm. An electrodehaving a thickness of 100 nm is formed thereon from a magnesium/silveralloy having a magnesium/silver mixing ratio of 10/1, to obtain anorganic EL device. The light-emitting layer is formed by depositionunder a vacuum of 10⁶ Torr at a substrate temperature of roomtemperature. The device shows emission having an excellent brightnessand efficiency at a direct current voltage of 5 V.

Application Example 3

Compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, are dissolvedin methylene chloride tetrahydrofuran, and the solution is spin-coatedon a cleaned glass substrate with an ITO electrode to form alight-emitting layer having a thickness of 50 nm. Then, aluminumbis(2-methyl-8-quinolinate)(2-naphtolate) is vacuum-deposited to form anelectron-injecting layer having a thickness of 10 nm, and an electrodehaving a thickness of 100 nm is formed thereon from a magnesium/aluminumalloy having a magnesium/aluminum mixing ratio of 10/1, to obtain anorganic EL device. The light-emitting layer and the electron-injectinglayer are formed by deposition under a vacuum of 10⁶ Torr at a substratetemperature of room temperature. The device shows an emission having anexcellent brightness and efficiency at a direct current voltage of 5 V.

Application Example 4

Compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, arevacuum-deposited on a cleaned glass substrate with an ITO electrode toform a light-emitting layer having a thickness of 50 nm. Then, aluminumtris(8-hydroxyquinolinate) is vacuum-deposited to form anelectron-injecting layer having a thickness of 10 nm and an electrodehaving a thickness of 100 nm is formed thereon from an aluminum/lithiumalloy having an aluminum/lithium mixing ratio of 50/1, to obtain anorganic EL device. A hole-injecting layer and the light-emitting layerare formed by deposition under a vacuum of 10⁶ Torr at a substratetemperature of room temperature. The device shows a light emissionhaving an excellent brightness and efficiency at a direct currentvoltage of 5 V.

Application Example 5

One of hole-injecting materials (H-1) to (H-6) is vacuum-deposited on acleaned glass substrate with an ITO electrode, to form a hole-injectinglayer having a thickness of 30 nm. Then, one of light-emitting materialsA1, A2, A3, B1, B2, C1, G1 and H1, respectively is vacuum-deposited toform a light-emitting layer having a thickness of 30 nm. Further, one ofelectron-injecting materials (E-1) to (E-6) is vacuum-deposited to forman electron-injecting layer having a thickness of 30 nm. An electrodehaving a thickness of 150 nm is formed thereon from a magnesium/silveralloy having a magnesium/silver mixing ratio of 10/1, to obtain anorganic EL device. Each layer is formed under a vacuum of 10⁶ Torr at asubstrate temperature of room temperature. All the organic EL devicesobtained in these Examples shows high brightness and efficiency.

Application Example 6

On a cleaned glass substrate with an ITO electrode,4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine isvacuum-deposited to form a first hole-injecting layer having a thicknessof 25 nm. Further, a hole-injecting material (H-1) is vacuum-depositedto form a second hole-injecting layer having a thickness of 5 nm. Then,compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, aslight-emitting materials are vacuum-deposited to form a light-emittinglayer having a thickness of 20 nm. Further, an electron-injectingmaterial (E-1) is vacuum-deposited to form an electron-injecting layerhaving a thickness of 30 nm. Then, an electrode having a thickness of150 nm is formed thereon from a magnesium/silver alloy having anmagnesium/silver mixing ratio of 10/1, to obtain an organic EL device.The device shows emission having an outstanding brightness andefficiency at a direct current voltage of 5 V.

Application Example 7

On a cleaned glass substrate with an ITO electrode,4,4′,4″-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine isvacuum-deposited to form a first hole-injecting layer having a thicknessof 25 nm. Further, a hole-injecting material (H-2) is vacuum-depositedto form a second hole-injecting layer having a thickness of 5 nm. Then,compounds A1, A2, A3, B1, B2, C1, G1 and H1, respectively, aslight-emitting materials are vacuum-deposited to form a light-emittinglayer having a thickness of 20 nm. Further, an electron-injectingmaterial (E-5) is vacuum-deposited to form an electron-injecting layerhaving a thickness of 30 nm. Then, an electrode having a thickness of150 nm is formed thereon from a magnesium/silver alloy having anmagnesium/silver mixing ratio of 10/1, to obtain an organic EL device.The device shows an emission having a outstanding brightness andefficiency at a direct current voltage of 5V.

Application Example 8

A hole-injecting material (H-5) is vacuum-deposited on a cleaned glasssubstrate with an ITO electrode to form a hole-injecting layer having athickness of 20 nm. Then, compounds A1, A2, A3, B1, B2, C1, G1 and H1,respectively, as light-emitting materials are vacuum-deposited to form alight-emitting layer having a thickness of 20 nm. Further, anelectron-injecting material (E-2) is vacuum-deposited to form a firstelectron-injecting layer having a thickness of 20 nm. Then, anelectron-injecting material (E-5) is vacuum-deposited to form a secondelectron-injecting layer having a thickness of 10 nm, and an electrodehaving a thickness of 150 nm is formed thereon from a magnesium/silveralloy having an magnesium/silver mixing ratio of 10/1, to obtain anorganic EL device. The device shows light emission having an excellentbrightness and efficiency at a direct current voltage of 5 V.

Application Example 9

An organic EL device is prepared in the same manner as in Example 5except that the light-emitting layer is replaced with a 30 nm thicklight-emitting layer formed by vacuum-depositing compounds A1, A2, A3,B1, B2, C1, G1 and H1, respectively, and one of the dopant compounds(D-1) to (D-7) in a weight ratio of 100:1. All the organic EL devicesobtained in these Examples shows high brightness characteristics andgives intended light emission colors.

Application Example 10

An organic EL device is prepared in the same manner as in Example 5except that the light-emitting layer is replaced with a 30 nm thicklight-emitting layer formed by vacuum-depositing compounds A1, A2, A3,B1, B2, C1, G1 and H1, respectively and one of Compounds (D-1) to (D-7)in a weight ratio of 100:1. All the organic EL devices obtained in theseExamples shows high brightness characteristics, or a maximum brightnessand gives intended light emission colors.

Application Example 11

A hole-injecting material (H-2) is vacuum-deposited on a cleaned glasssubstrate with an ITO electrode to form a hole-injecting layer having athickness of 30 nm. Then, 4,4′-bis(α,α-diphenylvinyl)biphenyl and alight-emitting material selected from compounds A1, A2, A3, B1, B2, C1,G1 and H1 for a light-emitting layer are vacuum-deposited in a weightratio of 100:5 to form a light-emitting layer having a thickness of 30nm. Further, an electron-injecting material (E-3) is vacuum-deposited toform an electron-injecting layer having a thickness of 30 nm. Then, anelectrode having a thickness of 150 nm is formed thereon from amagnesium/silver alloy having an magnesium/silver mixing ratio of 10/1,to obtain an organic EL device. The device shows an emission having anoutstanding brightness and efficiency at a direct current voltage of 5V.

Application Example 12

An organic EL device is prepared in the same manner as in Example 11except that the light-emitting layer is replaced with a 30 nm thicklight-emitting layer formed by vacuum-depositing aluminumtris(8-hydroxyquinolinate) and one of the light-emitting materials A1,A2, A3, B1, B2, C1, G1 and H1 in a weight ratio of 100:3. All theorganic EL devices obtained in these Examples shows high brightnesscharacteristics at a direct current of 5 V.

The organic EL devices obtained in the Application Examples of thepresent invention show an excellent light emission brightness andachieved a high light emission efficiency. When the organic EL devicesobtained in the above Examples are allowed to continuously emit light at3 (mA/cm²), all the organic EL devices remain stable. Since thelight-emitting materials of the present invention have a very highfluorescence quantum efficiency, the organic EL devices using thelight-emitting materials achieved light emission with a high brightnessin a low electric current applied region, and when the light-emittinglayer additionally uses a doping material, the organic EL devices areimproved in maximum light emission brightness and maximum light emissionefficiency. Further, by adding a doping material having a differentfluorescent color to the light-emitting material of the presentinvention, there are obtained light-emitting devices having a differentlight emission color. The organic EL devices of the present inventionaccomplish improvements in light emission efficiency and light emissionbrightness and a longer device life, and does not impose any limitationson a light-emitting material, a dopant, a hole-injecting material, anelectron-injecting material, a sensitizer, a resin and an electrodematerial used in combination and the method of producing the device. Theorganic EL device using the material of the present invention as alight-emitting material achieves light emission having a high brightnesswith a high light emission efficiency and a longer life as compared withconventional devices. According to the light-emitting material of thepresent invention and the organic EL device of the present invention,there can be achieved an organic EL device having a high brightness, ahigh light emission efficiency and a long life.

1-16. (canceled)
 17. A compound of formula (I)

wherein V is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, which can be substituted orunsubstituted, H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₁₈alkenyl,C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D; —SR⁵; —NR⁵R⁶; W is C₆-C₃₀aryl or C₂-C₃₀heteroaryl,which can be substituted or unsubstituted, H C₁-C₁₈alkyl; C₁-C₁₈alkylwhich is optionally substituted by E and optionally interrupted by D;C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is optionally substituted by E andoptionally interrupted by D: C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which isoptionally substituted by E and optionally interrupted by D;C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is optionally substituted by E andoptionally interrupted by D; —SR⁵; —NR⁵R⁶; Y is C₆-C₃₀aryl orC₂-C₃₀heteroaryl, which can be substituted or unsubstituted, H,C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionally substituted by E andoptionally interrupted by D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which isoptionally substituted by E and optionally interrupted by D;C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionally substituted by E andoptionally interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which isoptionally substituted by E and optionally interrupted by D; —SR⁵;—NR⁵R⁶; X is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, which can be substituted orunsubstituted, H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₁₈alkenyl,C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D; —SR⁵; —NR⁵R⁶; or one or more of the substituents V, W,X, or Y is a group of the formula —Z or —Ar—Z, wherein Ar is

wherein Z is a group of formula

wherein A¹, B¹ and B² are independently of each other H; C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which isoptionally substituted by E and optionally interrupted by D;C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is optionally substituted by Eand optionally interrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which isoptionally substituted by E and optionally interrupted by D;C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionally substituted by E andoptionally interrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which isoptionally substituted by E and optionally interrupted by D; —SR⁵;—NR⁵R⁶; C₂-C₁₈heteroaryl; C₂-C₁₈heteroaryl which is substituted by L;—SOR⁴; —SO₂R⁴; —COR⁸; —COOR⁷; —CONR⁵R⁶; C₄-C₁₈cycloalkyl;C₄-C₁₈cycloalkyl which is optionally substituted by E and optionallyinterrupted by D; C₄-C₁₈cycloalkenyl; C₄-C₁₈cycloalkenyl which isoptionally substituted by E and optionally interrupted by D; wherein twosubstituents A¹, B¹, B² or B¹ and B² optionally form a five to sevenmembered ring, which is optionally substituted, m is an integer of 1 to4; D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; —SiR⁵R⁶—;—POR⁵—; —CR⁵═CR⁶—; or —C≡C—; E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷;—CONR⁵R⁶; —CN; —OCOOR⁷; or halogen; G is E; K; heteroaryl; heteroarylwhich is substituted by C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by Eand/or K; K is C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionally substitutedby E and optionally interrupted by D; C₇-C₁₈alkylaryl which isoptionally substituted by E and optionally interrupted by D;C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is optionally substituted by E andoptionally interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which isoptionally substituted by E and optionally interrupted by D;C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is optionally substituted by E andoptionally interrupted by D; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which isoptionally substituted by E and optionally interrupted by D;C₄-C₁₈cycloalkenyl; or C₄-C₁₈cycloalkenyl which is optionallysubstituted by E and optionally interrupted by D; L is E; K; C₆-C₁₈aryl;or C₆-C₁₈aryl which is substituted by G, E and/or K; R⁴ is C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy;C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—; R⁵ and R⁶ areindependently of each other H; C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; C₁-C₁₈alkyl; or C₁-C₁₈alkylwhich is interrupted by —O—; wherein R⁵ and R⁶ optionally together forma five or six membered ring R⁷ is H; C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; C₁-C₁₈alkyl; C₁-C₁₈alkyl whichis interrupted by —O—; R⁸ is H; C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; C₁-C₁₈alkyl; C₁-C₁₈alkyl whichis interrupted by —O—; with the proviso that at least one of the groupsV, W, X and Y is a C₆-C₂₄aryl, or C₂-C₂₄heteroaryl group, which isoptionally substituted.
 18. The compound of claim 17, wherein W, X, andY are each C₆-C₃₀aryl or C₂-C₃₀heteroaryl; at least one of the groups W,X, and Y is represented by

wherein R¹¹, R^(11′), R¹², R^(12′), R¹³, R^(13′), R¹⁵, R^(15′), R¹⁶,R^(16′), R¹⁷, and R^(17′) are independently of each other H, E,C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by E; C₁-C₁₈alkyl;C₁-C₁₈alkyl which is optionally substituted by E and optionallyinterrupted by D; C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which is substitutedby E; the substituent pairs R^(11′) and R¹², R^(12′) and R¹³, R^(15′)and R¹⁶, and R^(16′) and R¹⁷ are each optionally a divalent groupselected from an oxygen atom, an sulfur atom, >CR¹¹⁸R¹¹⁹, >SiR¹¹⁸R¹¹⁹,and

wherein R¹¹⁸ and R¹¹⁹ are independently of each other C₁-C₁₈alkyl;C₁-C₁₈alkoxy, C₆-C₁₈aryl; C₇-C₁₈aralkyl; R⁴⁹ and R⁵⁰ are independentlyof each other H, C₁-C₁₈alkyl; C₁-C₁₈alkyl, which is optionallysubstituted by E and optionally interrupted by D; E; C₆-C₁₈aryl;C₆-C₁₈aryl, which is substituted by E; and the substituent pairs R¹¹ andR^(11′), R¹² and R^(12′), R¹³ and R^(13′), R^(13′) and R¹⁴, R¹⁴ and R¹⁵,R¹⁵ and R^(15′), R¹⁶ and R^(16′), and R^(17′) and R¹⁷, are eachoptionally the divalent group

wherein R³⁰, R³¹, R³², and R³³ are independently of each other H,C₁-C₁₈alkyl; C₁-C₁₈alkyl, which is optionally substituted by E andoptionally interrupted by D; E; C₆-C₁₈aryl; C₆-C₁₈aryl, which issubstituted by E; R¹⁴ is H, C₂-C₃₀heteroaryl, C₆-C₃₀aryl, or C₆-C₃₀arylwhich is substituted by E, C₁-C₁₈alkyl; or C₁-C₁₈alkyl which isoptionally substituted by E and optionally interrupted by D; D is —CO—;—COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; SiR⁵R⁶—; —POR⁵—;—CR⁹═CR¹⁰—; or —C≡C—; E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —CONR⁵R⁶;—CN; or halogen, especially F, or Cl; wherein R⁵ and R⁶ areindependently of each other C₆-C₁₈aryl; C₆-C₁₈aryl which is substitutedby C₁-C₁₈alkyl, C₁-C₁₈alkyl; or C₆-C₁₈alkyl which is interrupted by —O—;wherein R⁵ and R⁶ together optionally form a five or six membered ring,R⁷ is C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—; R⁸ isC₇-C₁₂alkylaryl; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by—O—; and R⁹ and R¹⁰ are independently of each other H, C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkyl; orC₁-C₁₈alkyl which is interrupted by —O—.
 19. The compound of claim 17,wherein W and Y are independently


20. The compound of claim 17, wherein V is H; W and Y are independently

and X is


21. The compound of claim 17, wherein V is

C₂-C₃₀heteroaryl, H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₁₈alkenyl,C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D: —SR⁵; or —NR⁵R⁶; X is

C₂-C₃₀heteroaryl, H, C₂-C₃₀heteroaryl, C₁-C₁₈alkyl; C₁-C₁₈alkyl which isoptionally substituted by E and optionally interrupted by D;C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which is optionally substituted by E andoptionally interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which isoptionally substituted by E and optionally interrupted by D;C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which is optionally substituted by E andoptionally interrupted by D; —SR⁵; or —NR⁵R⁶ W is

Y is

C₂-C₃₀heteroaryl, H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₁₈alkenyl,C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D: —SR⁵; or —NR⁵R⁶; wherein the groups V¹ to V⁵, W¹ toW⁵, X¹ to X⁵ and Y¹ to Y⁵ are each independently H; halogen, C₆-C₂₄aryl;C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which isoptionally substituted by E and optionally interrupted by D;C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is optionally substituted by Eand optionally interrupted by D; C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which isoptionally substituted by E and optionally interrupted by D;

wherein Ar¹ is C₆-C₃₀aryl or C₂-C₃₀heteroaryl, especially phenyl, Ar² isC₆-C₃₀aryl or C₂-C₃₀heteroaryl, especially phenyl, or H, C₂-C₁₈alkynyl;C₂-C₁₈alkynyl which is optionally substituted by E and optionallyinterrupted by D; C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is optionallysubstituted by E and optionally interrupted by D; —SR⁵; —NR⁵R⁶;C₂-C₂₄heteroaryl; C₂-C₂₄heteroaryl which is substituted by L; —SOR⁴;—SO₂R⁴; —COR⁸; —COOR⁷; —CONR⁵R⁶; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkylwhich is optionally substituted by E and optionally interrupted by D;C₄-C₁₈cycloalkenyl; C₄-C₁₈cycloalkenyl which is optionally substitutedby E and optionally interrupted by D; or W⁵ or Y⁵ together with V form agroup —CR⁹ ₂—, —CR⁹ ₂—CR⁹ ₂—, —C(═O)CR⁹ ₂—, —C(═O)—, or —CR⁹═CR⁹—, or W⁵and Y⁵ together with V form a group

wherein R⁹ is H; C₁-C₁₈alkyl, C₁-C₁₈alkyl which is interrupted by —O—,C₆-C₁₈aryl, C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl, orC₁-C₁₈alkoxy, or one or more of the substituents V¹ to V⁵, W¹ to W⁵, X¹to X⁵, or Y¹ to Y⁵ is a group of the formula —Z′ or —Ar—Z′, wherein Aris

wherein Z′ is a group of formula

wherein two adjacent substituents V¹ to V⁵, W¹ to W⁵, X¹ to X⁵, or Y¹ toY⁵ optionally join to form a five to seven membered ring.
 22. Thecompound of claim 21, wherein W is

X is

and Y is


23. The compound of claim 21, wherein the compound is represented byformula (IV)

wherein V is H or C₁-C₁₈ alkyl; W¹, W⁵, Y¹, Y⁵, X¹, and X⁵ areindependently of each other H; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which isoptionally substituted by E and optionally interrupted by D; and W³, X³and Y³ are selected from the group consisting of C₆-C₂₄aryl, C₆-C₂₄arylwhich is substituted by G, C₂-C₂₄heteroaryl, C₂-C₂₄heteroaryl which issubstituted by L, C₁-C₁₈alkoxy, —SR⁵, and —NR⁵R⁶.
 24. The compound ofclaim 21, wherein the compound is represented by formula (Xa) or (Xb)

wherein V is H or C₁-C₈alkyl; X³ and X⁴ are independently of each otherH, C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈thioalkyl, or phenyl, X⁵ is H orC₁-C₈alkoxy; W⁵ is H, C₁-C₈alkyl, or O(CH₂)_(n1)—X; Y⁵ is H, C₁-C₈alkyl,or O(CH₂)_(n1)—X; Y³, Y⁴, W³, and W⁴ are independently of each otherC₁-C₈alkyl; C₁-C₈alkoxy; C₁-C₈thioalkyl; halogen; phenyl; orO(CH₂)_(n1)—X; each occurrence of n1 is independently an integer of 1 to5; each X is independently —O—(CH₂)_(m1)CH₃, —OC(O)—(CH₂)_(m1)CH₃,—C(O)—O—C₁-C₈alkyl, or —NR¹⁰³R¹⁰⁴; wherein m1 is an integer of 0 to 5;and R¹⁰³ and R¹⁰⁴ are independently of each other H or C₁-C₈-alkyl,wherein R¹⁰³ and R¹⁰⁴together optionally form a five or six memberedheterocyclic ring.
 25. The compound of claim 21, wherein the compound isrepresented by formula (XI)

wherein V is H, or C₁-C₈alkyl; W³ is H, C₁-C₈alkyl, or C₁-C₈alkoxy; X³is H, C₁-C₈alkoxy, phenyl or O(CH₂)_(n1)—X; X⁵ is H, C₁-C₈alkoxy, phenylor O(CH₂)_(n1)—X; Y³ is H, C₁-C₈alkyl, or C₁-C₈alkoxy; each occurrenceof n1 is independently an integer of 1 to 5; each X is independently—O—(CH₂)_(m1)CH₃, —OC(O)—(CH₂)_(m1)CH₃, —C(O)—O—C₁-C₈alkyl, or—NR¹⁰³R¹⁰⁴; wherein m1 is an integer of 0 to 5; and R¹⁰³ and R¹⁰⁴ areindependently of each other H or C₁-C₈-alkyl, wherein R¹⁰³ and R¹⁰⁴together optionally form a five or six membered heterocyclic ring. 26.The compound of claim 21, wherein the compound is represented by formula(XIVa), (XIVb), (XIVc), (XIVd), or (XIVe):

wherein each R⁹ is independently H; C₁-C₁₈alkyl, C₁-C₁₈alkyl which isinterrupted by —O—, C₆-C₁₈aryl, C₆-C₁₈aryl which is substituted byC₁-C₁₈alkyl, or C₁-C₁₈alkoxy.
 27. The compound of claim 21, wherein thecompound is represented by formula (XVIII)

wherein W³ and Y³ are a group of formula

wherein each occurrence of R¹¹⁰ is C₄-C₁₀-heteroaryl, phenyl,1-naphthyl, 2-naphthyl, 3-biphenyl, 4-biphenyl, 9-phenanthryl,2-fluorenyl, or 9-fluorenyl; each of which is optionally substituted byC₁-C₆-alkyl or C₁-C₄-alkoxy; and X³ is H, C₁-C₆-alkyl, C₁-C₄-alkoxy,phenyl, or


28. The compound of 21, wherein the compound is represented by one ofcompound A-1 to A-52:

Cpd. X³ Y³ W³ X⁵ Y¹ W⁵ V A-1 H OCH₂COOMe OCH₂COOMe H OCH₂COOMe OCH₂COOMeH A-2 Ph OCH₂COOMe OCH₂COOMe H OCH₂COOMe OCH₂COOMe H A-3 H OMe OMe H H HH A-4 H Ph Ph H H H H A-5 H OMe OMe H OMe OMe H A-6 H OBu OBu H H H HA-7 H OBu OBu H OBu OBu H A-8 OMe OMe OMe OMe OMe OMe H A-9 OMe Br BrOMe H H H A-10 Ph Br Br H H H H A-11 OMe Ph Ph OMe H H H A-12 Ph Ph Ph HH H H A-13 SMe SMe SMe H H H H A-14 H SMe SMe H H H H A-15 H OCH₂CH₂OAcOCH₂CH₂OAc H H H H A-16 H OCH₂CH₂OAc OCH₂CH₂OAc H OCH₂CH₂OAc OCH₂CH₂OAcH A-17 H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et H H H H A-18 H OCH₂CH₂OCH₂EtOCH₂CH₂OCH₂Et H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et H A-19 H N(CH₃)₂ N(CH₃)₂ H HH H A-20 H

H H H H A-21 Ph N(CH₃)₂ N(CH₃)₂ H H H H A-22 Ph

H H H H A-23 H CH₃ CH₃ H H H H A-24 Ph CH₃ CH₃ H H H H A-25 Ph Ph Ph H HH CH₃ A-26 OMe OMe OMe H H H CH₃ A-27 H Ph Ph H H H CH₃ A-28 H OMe OMe HH H CH₃ A-29 H OMe OMe H OMe OMe CH₃ A-30 H OBu OBu H H H CH₃ A-31 H OBuOBu H OBu OBu CH₃ A-32 OMe OMe OMe OMe OMe OMe CH₃ A-33 OMe Br Br OMe HH CH₃ A-34 Ph Br Br H H H CH₃ A-35 OMe Ph Ph. OMe H H CH₃ A-36 HOCH₂COOMe OCH₂COOMe H OCH₂COOMe OCH₂COOMe CH₃ A-37 SMe SMe SMe H H H CH₃A-38 H SMe SMe H H H CH₃ A-39 H OCH₂CH₂OAc OCH₂CH₂OAc H H H CH₃ A-40 HOCH₂CH₂OAc OCH₂CH₂OAc H OCH₂CH₂OAc OCH₂CH₂OAc CH₃ A-41 H OCH₂CH₂OCH₂EtOCH₂CH₂OCH₂Et H H H CH₃ A-42 H OCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et HOCH₂CH₂OCH₂Et OCH₂CH₂OCH₂Et CH₃ A-43 OBu Ph Ph OBu H H CH₃ A-44 HN(CH₃)₂ N(CH₃)₂ H H H CH₃ A-45 H

H H H CH₃ A-46 Ph N(CH₃)₂ N(CH₃)₂ H H H CH₃ A-47 Ph

H H H CH₃ A-48 Ph CH₃ CH₃ H H H CH₃ A-49 Ph CH₃ CH₃ H H H CH₃ A-50 OMeOMe OMe H H H H A-51 H H H H H H H A-52 Ph H H H H H H.


29. The compound of claim 21, wherein the compound is represented by oneof compound B-1 to B-23:

Cpd. X³ V³ W³ X⁵ V B-1 Ph H H H H B-2 H H H H H B-3 OBu H H OBu H B-4OMe H H OMe H B-5 OCH₂COOMe H H OCH₂COOMe H B-6 H OMe OMe H H B-7OCH₂CH₂OCH₂Et H H OCH₂CH₂OCH₂Et H B-8 OCH₂CH₂OAc H H OCH₂CH₂OAc H B-9OMe OMe OMe OMe H B-10 OMe OMe OMe OMe H B-11 H CH₃ CH₃ H H B-12 Ph CH₃CH₃ H H B-13 Ph H H H CH₃ B-14 OMe H H OMe CH₃ B-15 OBu H H OBu CH₃ B-16H H H H CH₃ B-17 OCH₂COOMe H H OCH₂COOMe CH₃ B-18 H OMe OMe H CH₃ B-19OCH₂CH₂OCH₂Et H H OCH₂CH₂OCH₂Et CH₃ B-20 OCH₂CH₂OAc H H OCH₂CH₂OAc CH₃B-21 H CH₃ CH₃ H CH₃ B-22 Ph CH₃ CH₃ H CH₃.


30. The compound of 21, wherein the compound is represented by one ofthe following compounds:


31. The compound of claim 21, wherein the compound is represented by oneof compound K-1 to K-16:

Cpd. Ar Cpd. Ar K-1

K-2

K-3

K-4

K-5

K-6

K-7

K-8

K-9

K-10

K-11

K-12

K-13

K-14

K-15

K-16


32. The compound of claim 17, wherein the compound is represented byformula (III)

wherein X and Y are each independently selected from the groupconsisting of C₆-C₃₀aryl or C₂-C₃₀heteroaryl which can be substituted orunsubstituted, H, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₁₈alkenyl,C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D; —SR⁵; and —NR⁵R⁶; if X is

then Y is R¹, or if Y is

then X is R¹; R¹ is H; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₈alkenyl;C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D; —SR⁵; or —NR⁵R⁶; V is H, C₆-C₃₀aryl orC₂-C₃₀heteroaryl, which can be substituted or unsubstituted;C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionally substituted by E andoptionally interrupted by D; C₂-C₁₈alkenyl, C₂-C₁₈alkenyl which isoptionally substituted by E and optionally interrupted by D:C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionally substituted by E andoptionally interrupted by D; C₁-C₁₈alkoxy; C₁-C₁₈alkoxy which isoptionally substituted by E and optionally interrupted by D; —SR⁵; or—NR⁵R⁶; W¹ to W⁵, X¹ to X⁵ and Y¹ to Y⁵ are independently of each otherH; C₆-C₂₄aryl; C₆-C₂₄aryl which is substituted by G; C₁-C₁₈alkyl;C₁-C₁₈alkyl which is optionally substituted by E and optionallyinterrupted by D; C₇-C₁₈alkylaryl; C₇-C₁₈alkylaryl which is optionallysubstituted by E and optionally interrupted by D; C₂-C₁₈alkenyl;C₂-C₁₈alkenyl which is optionally substituted by E and optionallyinterrupted by D;

wherein Ar¹ is C₆-C₃₀aryl or C₂-C₃₀heteroaryl and Ar² is C₆-C₃₀aryl orC₂-C₃₀heteroaryl; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which is optionallysubstituted by E and optionally interrupted by D; C₁-C₁₈alkoxy;C₁-C₁₈alkoxy which is optionally substituted by E and optionallyinterrupted by D; —SR⁵; —NR⁵R⁶; C₂-C₂₄heteroaryl; C₂-C₂₄heteroaryl whichis substituted by L; —SOR⁴; —SO₂R⁴; —COR⁸; —COOR⁷; —CONR⁵R⁶;C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which is optionally substituted by Eand optionally interrupted by D; C₄-C₁₈cycloalkenyl; orC₄-C₁₈cycloalkenyl which is optionally substituted by E and optionallyinterrupted by D; wherein two adjacent substituents selected from V, W¹to W⁵, X¹ to X⁵, and Y¹ to Y⁵ optionally join to form a five to sevenmembered ring; D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—, —NR⁵—;—SiR⁵R⁶—; —POR⁵—; —CR⁵═CR⁶— or —C≡C—; E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸;—COOK′; —CONR⁵R⁶; —CN; —OCOOR⁷ or halogen; G is E; K; heteroaryl;heteroaryl which is substituted by C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by E or K; K is C₁-C₁₈alkyl; C₁-C₁₈alkyl which is optionallysubstituted by E and optionally interrupted by D; C₇-C₁₈alkylaryl whichis optionally substituted by E and optionally interrupted by D;C₂-C₁₈alkenyl; C₂-C₁₈alkenyl which is optionally substituted by E andoptionally interrupted by D; C₂-C₁₈alkynyl; C₂-C₁₈alkynyl which isoptionally substituted by E and optionally interrupted by D;C₁-C₁₈alkoxy, C₁-C₁₈alkoxy which is optionally substituted by E andoptionally interrupted by D; C₄-C₁₈cycloalkyl; C₄-C₁₈cycloalkyl which isoptionally substituted by E and optionally interrupted by D;C₄-C₁₈cycloalkenyl; or C₄-C₁₈cycloalkenyl which is optionallysubstituted by E and optionally interrupted by D; L is E; K; C₆-C₁₈arylor C₆-C₁₈aryl which is substituted by G, E or K; R⁴ is C₆-C₁₈aryl;C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl or C₁-C₁₈alkoxy;C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by —O—; R⁵ and R⁶ areindependently of each other H; C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by C₁-C₁₈alkyl or C₁-C₁₈alkoxy; C₁-C₁₈alkyl; or C₁-C₁₈alkylwhich is interrupted by —O—; or R⁵ and R⁶ together form a five or sixmembered ring; R⁷ is H; C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted byC₁-C₁₈alkyl or C₁-C₁₈alkoxy; C₁-C₁₈alkyl; C₁-C₁₈alkyl which isinterrupted by —O—; R⁸ is H; C₆-C₁₈aryl; C₆-C₁₈aryl which is substitutedby C₁-C₁₈alkyl or C₁-C₁₈alkoxy; C₁-C₁₈alkyl; C₁-C₁₈alkyl which isinterrupted by —O—.
 33. An electroluminescent device comprising thecompound of claim
 17. 34. An electroluminescent device comprising thecompound of claim
 21. 35. An electroluminescent device comprising thecompound of claim
 22. 36. An electroluminescent device comprising thecompound of claim 32.